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  1. #1
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    Arecoline: Full Information (CNS Stimulant,ect.)

    Arecoline

    From Wikipedia, the free encyclopedia


    Arecoline
    Systematic (IUPAC) name
    methyl1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
    Identifiers
    CAS number 63-75-2
    ATC code ?
    PubChem 2230
    DrugBank EXPT03296
    Chemical data
    Formula C8H13NO2
    Mol. mass 155.194 g/mol
    SMILES search in eMolecules, PubChem
    Physical data
    Density 1.0495 g/cm?
    Boiling point 209 ?C (408 ?F)
    Pharmacokinetic data
    Bioavailability ?
    Metabolism ?
    Half life ?
    Excretion ?
    Therapeutic considerations
    Pregnancy cat.

    ?
    Legal status
    Routes ?

    Arecoline is an alkaloid-type natural product found in betel nuts from the betel palm (Areca catechu).[1] It is an oily liquid that is soluble in water, alcohols, and ether.

    Mechanism

    In many Asian cultures, the betel nut is chewed to obtain a stimulating effect. Arecoline is the primary active ingredient responsible for the central nervous system effects which are roughly comparable to those of nicotine, which has a similar chemical structure. Arecoline is known to be an agonist of muscarinic acetylcholine M1, M2 and M3 receptors,[1][2][3] which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.).

    Uses

    Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, [4] it is not the first drug of choice for this degenerative disease. [5]

    Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).[6]

    References

    1. ^ a b Ghelardini C, Galeotti N, Lelli C, Bartolini A. (2001). "Arecoline M1 receptor activation is a requirement for arecoline analgesia.". Farmaco. 56 (5?7): 383?5. PMID 11482763.
    2. ^ Yang YR, Chang KC, Chen CL, Chiu TH. (2000). "Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.". Chin J Physiol. 43 (1): 23?8. PMID 10857465.
    3. ^ Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. (2004). "Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.". Chin J Physiol. 47 (2): 89?94. PMID 15481791.
    4. ^ Saikia JR, Schneeweiss FH, Sharan RN. (1999). "Arecoline-induced changes of poly-ADP-ribosylation of cellular proteins and its influence on chromatin organization.". Cancer Letters. 139 (1): 59?65. PMID 10408909.
    5. ^ Christie JE, Shering A, Ferguson J (1981). "Physostigmine and arecoline: effects of intravenous infusions in Alzheimer?s presenile dementia". British Journal of Psychiatry 138: 46?50. PMID 7023592.
    6. ^ Yusuf H, Yong SL (2002). "Oral submucous fibrosis in a 12-year-old Bangladeshi boy: a case report and review of literature". International journal of paediatric dentistry / the British Paedodontic Society [and] the International Association of Dentistry for Children 12 (4): 271-6. PMID 12121538.
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    I found a source selling an extract of this which states

    "Caution 10-20mg is equal to a daily dose of caffeine!"

    Its Arecolin HBR 99% (Areca Catechu Isolate, betal nut)

    I actually used a betal nut product and enjoyed the effects, stimulating and felt pretty good. It was a ground betal nut mixture from india with spices.

    But this stuff I just found looks extremely potent.
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    parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.)

    possible carcinogenic properties

    Interesting.
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    Arecoline

    CAS Type 1 Name: 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester

    Equivalent Term: Methylarecaidin

    CAS Registry No. 63-75-2

    Description An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands. http://ctd.mdibl.org/detail.go;jsess...em&acc=D001115
    Last edited by NO HYPE; 01-02-2008 at 05:03 PM.
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    Thumbs down

    Toxicology. 2008 Jan 14;243(1-2):1-10. Epub 2007 Sep 8.

    Arecoline-induced growth arrest and p21(WAF1) expression are dependent on p53 in rat hepatocytes.

    Betel-quid use is associated with the risk of liver cirrhosis and hepatocellular carcinoma and arecoline, the major alkaloid of betel-quid, is hepatotoxic in mice. Therefore, we studied the cytotoxic and genotoxic effects of arecoline in normal rat hepatocytes (Clone-9 cells). Arecoline dose-dependently (0.1-1mM) decreased cell cycle-dependent proliferation while inducing DNA damage at 24h. Moreover, arecoline (1mM)-induced apoptosis and necrosis at 24h. Arecoline dose-dependently (0.1-0.5mM) increased transforming growth factor-beta (TGF-beta) mRNA, gene transcription and bioactivity and neutralizing TGF-beta antibody attenuated arecoline (0.5mM)-inhibited cell proliferation at 24h. Arecoline (0.5mM) also increased p21(WAF1) protein expression and p21(WAF1) gene transcription. Moreover, arecoline (0.5mM) time-dependently (8-24h) increased p53 serine 15 phosphorylation. Pifithrin-alpha (p53 inhibitor) and the loss of the two p53-binding elements in the p21(WAF1) gene promoter attenuated arecoline-induced p21(WAF1) gene transcription at 24h. Pifithrin-alpha also attenuated arecoline (0.5mM)-inhibited cell proliferation at 24h. We concluded that arecoline induces cytotoxicity, DNA damage, G(0)/G(1) cell cycle arrest, TGF-beta1, p21(WAF1) and activates p53 in Clone-9 cells. Moreover, arecoline-induced p21(WAF1) is dependent on p53 while arecoline-inhibited growth is dependent on both TGF-beta and p53.



    J Oral Pathol Med. 2001 Sep;30(8):458-64. Links

    Synergistic effects of nicotine on arecoline-induced cytotoxicity in human buccal mucosal fibroblasts.

    Areca quid chewing has been linked to oral submucous fibrosis and oral cancer. Arecoline, a major areca nut alkaloid, is considered to be the most important etiologic factor in the areca nut. In order to elucidate the pathobiological effects of arecoline, cytotoxicity assays, cellular glutathione S-transferase (GST) activity and lipid peroxidation assay were employed to investigate cultured human buccal mucosal fibroblasts. To date, there is a large proportion of areca quid chewers who are also smokers. Furthermore, nicotine, the major product of cigarette smoking, was added to test how it modulated the cytotoxicity of arecoline. At a concentration higher than 50 microg/ml, arecoline was shown to be cytotoxic to human buccal fibroblasts in a dose-dependent manner by the alamar blue dye colorimetric assay (P<0.05). In addition, arecoline significantly decreased GST activity in a dose-dependent manner (P<0.05). At concentrations of 100 microg/ml and 400 microg/ml, arecoline reduced GST activity about 21% and 46%, respectively, during a 24 h incubation period. However, arecoline at any test dose did not increase lipid peroxidation in the present human buccal fibroblast test system. The addition of extracellular nicotine acted synergistically on the arecoline-induced cytotoxicity. Arecoline at a concentration of 50 microg/ml caused about 30% of cell death over the 24 h incubation period. However, 2.5 mM nicotine enhanced the cytotoxic response and caused about 50% of cell death on 50 microg/ml arecoline-induced cytotoxicity. Taken together, arecoline may render human buccal mucosal fibroblasts more vulnerable to other reactive agents in cigarettes via GST reduction. The compounds of tobacco products may act synergistically in the pathogenesis of oral mucosal lesions in areca quid chewers. The data presented here may partly explain why patients who combined the habits of areca quid chewing and cigarette smoking are at greater risk of contracting oral cancer.
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  6. #6
    nom nom nom deserusan's Avatar
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    Arecoline is perfectly safe. The carcinogenic issues arise from the other constituents of the betel nut, not arecoline itself. I've reviewed a lot of the research and find this to be a very promising compound.

    -D
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    "a cyclin-dependent kinase (Cdk) inhibitor"

    "negative cell cycle regulator p21Waf1"

    "cholinergic muscarinic agonist"

    "p21WAF1/CIP1 selectively controls the transcriptional activity of estrogen receptor alpha."
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    nom nom nom deserusan's Avatar
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    Originally Posted by NO HYPE View Post
    "a cyclin-dependent kinase (Cdk) inhibitor"

    "negative cell cycle regulator p21Waf1"

    "cholinergic muscarinic agonist"

    "p21WAF1/CIP1 selectively controls the transcriptional activity of estrogen receptor alpha."
    You are missing the point here. Those studies are not using 100% arecoline. I suggest actually reading a full study on it before passing judgement based on abstracts.
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    Originally Posted by deserusan View Post
    Arecoline is perfectly safe. The carcinogenic issues arise from the other constituents of the betel nut, not arecoline itself. I've reviewed a lot of the research and find this to be a very promising compound.

    -D
    Thanks for the heads up des. I had not viewed this one until tonight. Plenty of in-vitro research.... not finding much relating to in-vivo human.
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    Originally Posted by deserusan View Post
    You are missing the point here.
    No des.... I just missed your post.
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  11. #11
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    Originally Posted by deserusan View Post
    I suggest actually reading a full study on it before passing judgement based on abstracts.
    Are you serious? I know how to read a study.... I'm not new to this.

    Passing judgement? Examples?

    I read EVERY full study that I can get my hands on.... and I gather what I can from abstracts.
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    Originally Posted by deserusan View Post
    I suggest actually reading a full study on it
    I am not the one who is interested in it.
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    Originally Posted by NO HYPE View Post
    Are you serious? I know how to read a study.... I'm not new to this.

    Passing judgement? Examples?
    Then read a study before commenting.
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    Originally Posted by deserusan View Post
    Then read a study before commenting.
    "Interesting." was my only comment.

    I posted what caught my eye.

    I never implied anything.
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    I guess my input here means nothing. Bye now.
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    Originally Posted by deserusan View Post
    Arecoline is perfectly safe. The carcinogenic issues arise from the other constituents of the betel nut, not arecoline itself. I've reviewed a lot of the research and find this to be a very promising compound.

    -D
    LOL.

    Originally Posted by NO HYPE View Post
    I guess my input here means nothing. Bye now.
    I dont think thats what he meant.
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    Originally Posted by NO HYPE View Post
    I guess my input here means nothing.
    Originally Posted by Sldge View Post
    LOL. I dont think thats what he meant.

    LOL.... I can read between the lines.


    Originally Posted by deserusan View Post
    I suggest actually reading a full study on it before passing judgement based on abstracts.
    Originally Posted by deserusan View Post
    read a study before commenting.
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    Arecolin Hbr 99% (Areca Catechu isolate, Betel nut)
    Arecolin Hbr 99%

    This is an extract of the primary active alkaloid in the stimulant known as Pinang, or Betel nut. It is the seed of the Betel palm (Areca catechu), native to the tropical Pacific, coastal Asia, and parts of eastern Africa. Very popular in many Asian countries, it is estimated that Betel nut is chewed by 10% of the world?s population.

    The effect of Betel nut is comparable (not identical) to caffeine; it is a mild, stimulating intoxicant. It is for these effects that the Betel nut has been popular in Asian culture for thousands of years. Pinang has a societal role similar to tobacco; it is used to bolster the body and mind during arduous work and is an integral part of such cultural ceremonies as weddings and religious worship. The traditional method of taking Pinang is to chew a mixture of shredded Betel nut mixed with lime, possibly with the addition of spices and tobacco. Unfortunately, persistent chewing of Betel nut causes a red staining of the gums and teeth and can even lead to cancer of the mouth and throat (especially when chewed with tobacco). [Studies have all but confirmed that the most detrimental effects of Betel nut stem from both heavy, regular use and the act of chewing the nut and its accompanying admixtures.]

    Arecoline itself has a history of medical use. It is the basis of many aphrodisiacs and anti-aging products, is prescribed as a remedy for intestinal parasites and worms, and is an active ingredient in traditional Asian preparations such as tooth powders. Modern clinical studies have been undertaken to determine whether Arecoline can be effective in such cases as improving nervous system response following cases of stroke or other cerebrovascular accidents, and even as a treatment for schizophrenia. Although contemporary medical study of this substance is still in its infancy, we hope to encourage progress by providing a carefully controlled extract of the Betel nut.

    CAUTION!!!!!!!!!!!!!

    This is extremely concentrated in comparrison to the raw material, 10mg-20mg is equal to approximately a daily dose of caffeine!


    ^^^^ from website offering it
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    Originally Posted by deserusan View Post
    Arecoline is perfectly safe. The carcinogenic issues arise from the other constituents of the betel nut, not arecoline itself. I've reviewed a lot of the research and find this to be a very promising compound.

    -D
    I wouldn't bet on its safety. It appears rather to be a 'mixed blessing'. on the one hand it displays anti-proliferative properties (e.g. cell cycle arrest, p53 activation) which can eventually be useful to inhibit growth of cancer cells.

    on the other hand, it induces DNA damage and is associated with upregulation of certain pro-oncogenes (e.g. c-jun), which can lead to pro-carcinogenic effects in healthy cells.

    It would be interesting to see whether healthy and malignant cells respond differently to different doses of arecoline.



    Oral Oncol. 2000 Sep;36(5):432-6. Links
    Induction of the c-jun protooncogene expression by areca nut extract and arecoline on oral mucosal fibroblasts.

    Ho TJ, Chiang CP, Hong CY, Kok SH, Kuo YS, Yen-Ping Kuo M.
    School of Dentistry, College of Medicine, National Taiwan University, 1 Chang-Te Street, 100, Taipei, Taiwan.

    To investigate the mechanisms of areca quid (AQ)-induced carcinogenesis, expression of c-fos and c-jun protooncogenes was examined in human oral mucosal fibroblasts after exposure to areca nut extracts (ANE) or arecoline. We found that treatment of cells with 200 microg/ml ANE or 10 microg/ml arecoline for 1 h induced about three-fold increase in c-jun mRNA levels. This increase was transient and the level of c-jun mRNAs returned rapidly to control levels thereafter. However, ANE and arecoline did not induce c-fos mRNA expression at detectable levels. During AQ chewing, oral mucosal cells are continuously stimulated by ANE and arecoline. Persistent induction of the c-jun protooncogene by ANE and arecoline may be one of the mechanisms in the carcinogenesis of oral squamous cell carcinoma in Taiwan. Furthermore, we observed that pre-incubation of cells with either N-acetyl-cysteine [a glutathione (GSH) precursor] or L-buthionine-S,R-sulfoximine (a specific inhibitor of GSH biosynthesis) had a minimal effect on arecoline-induced c-jun expression. Therefore, arecoline-induced c-jun expression is independent of GSH depletion.

    PMID: 10964049 [PubMed - indexed for MEDLINE]
    Last edited by Dr.P; 01-02-2008 at 11:42 PM.
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    Originally Posted by deserusan View Post
    .. The carcinogenic issues arise from the other constituents of the betel nut, not arecoline itself.
    well, the following study investigated betel nut extract and arecoline separately:

    J Biol Chem. 2004 Dec 3;279(49):50676-83.
    The induction of prostaglandin E2 production, interleukin-6 production, cell cycle arrest, and cytotoxicity in primary oral keratinocytes and KB cancer cells by areca nut ingredients is differentially regulated by MEK/ERK activation.

    Chang MC, Wu HL, Lee JJ, Lee PH, Chang HH, Hahn LJ, Lin BR, Chen YJ, Jeng JH.
    Team of Biomedical Science, Chang-Gung Institute of Technology, Kwei-Shan, Taoyuan, Taiwan.

    There are about 200-600 million betel quid (BQ) chewers in the world. BQ chewing is one of the major risk factor of hepatocarcinoma, oropharyngeal, and esophagus cancers in Taiwan, India, and Southeast Asian countries. Thus, the precise molecular mechanisms deserve investigation. We used cultured primary keratinocytes and KB cells, RT-PCR, flow cytometry, Western blotting, and ELISA to evaluate whether alterations in early gene expression is crucial in the carcinogenic processes of BQ. We observed the induction of c-Fos mRNA expression in human gingival keratinocyte (GK) and KB carcinoma cells by areca nut (AN) extract and arecoline. A maximal increment in c-fos gene expression was shown at about 30 min after challenge. AN extract (100-800 microg/ml) and arecoline (0.1-0.8 mM) also stimulated ERK1/ERK2 phosphorylation with a maximal stimulation at 5-10 min of exposure. Pretreatment by U0126 (30 microM), a MEK inhibitor, markedly inhibited the c-Fos, cyclooxygenase-2 (COX-2), and IL-6 mRNA expression of the KB epithelial cells. In addition, U0126 and PD98059 (50 microM) also decreased AN extract- and arecoline-associated PGE2 and IL-6 production in GK and KB cells. However, U0126 by itself arrested the cells in G0/G1 phase, but was not able to prevent AN- and arecoline-induced cell death or apoptosis. In contrast, U0126 enhanced the AN-induced apoptosis of KB cells. AN ingredients thus play a significant role in the pathogenesis of oropharyngeal cancer by activation of MEK1/ERK/c-Fos pathway, which promotes keratinocyte inflammation, cell survival, and affects cell cycle progression.
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    Originally Posted by Mike83 View Post
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    I can't comment on anything... I have not read a FULL study.
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    Print ISSN: 0300-5577
    Volume: 33 | Issue: 5
    Cover date: October 2005
    Page(s): 399-405


    Effects of arecoline in relaxing human umbilical vessels and inhibiting endothelial cell growth

    This study investigated the effects of arecoline, an active ingredient of the areca nut, on the tone of human umbilical arteries and veins and on the eNOS expression and cell proliferation of human umbilical vein endothelial cells (HUVECs). We found that arecoline relaxes the human umbilical artery and vein rings in a concentration-dependent manner; the higher the concentration of arecoline, the greater the relaxation of the rings. However, the relaxation decreases after the endothelium was removed or pretreated with L-NAME, a nitric oxide synthase inhibitor. Moreover, arecoline increases in a dose-dependent way the cGMP levels of human umbilical arteries and veins. In HUVECs, arecoline also increases the eNOS expression. Therefore, the relaxant effects of arecoline on the umbilical artery and vein rings were endothelium-dependent through the NO-cGMP systems. In addition, arecoline at higher doses (100?1000 μM) inhibits endothelial cell proliferation; the exposure toarecoline (100?1000 μM) for 24 and 48 h induces G2/M cell cycle arrest of HUVECs. Our results indicate that arecoline would decrease vascular tone, in part mediated by NO. Higher doses of arecoline inhibit endothelial cell growth, which suggest that long-term use or high doses of areca nut might induce endothelial dysfunction and associated diseases.http://www.atypon-link.com/WDG/doi/a...urnalCode=jpme
    Last edited by NO HYPE; 01-03-2008 at 02:31 AM.
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    As alluded to before, are they using pure arecoline or an extract with arecoline in it? There is a big difference especially when it comes to betel.
    "I just use my muscles as a conversation piece, like someone walking a cheetah down 42nd Street." - Arnold Schwarzenegger

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    Originally Posted by deserusan View Post
    As alluded to before, are they using pure arecoline or an extract with arecoline in it? There is a big difference especially when it comes to betel.

    with regards to the studies I cited above, they examined betel extract AND arecoline separately.
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    Originally Posted by deserusan View Post
    As alluded to before, are they using pure arecoline or an extract with arecoline in it?
    You did not allude to anything previously.... you stated that they were not using pure arecoline.

    Why is this not considered pure?
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    Originally Posted by deserusan View Post
    As alluded to before, are they using pure arecoline or an extract with arecoline in it?
    Where was anything mentioned about an extract?

    I keep seeing the word 'arecoline'.... not 'a mixture of arecholine'.
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    Originally Posted by Dr.P View Post
    with regards to the studies I cited above, they examined betel extract AND arecoline separately.
    What was the standardization and was this pure arecoline?

    Originally Posted by NO HYPE View Post
    You did not allude to anything previously.... you stated that they were not using pure arecoline.

    Why is this not considered pure?
    Pure arecoline is 100% arecoline with no impurities. Is that what they were using?
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    Originally Posted by deserusan View Post
    What was the standardization and was this pure arecoline?



    Pure arecoline is 100% arecoline with no impurities. Is that what they were using?
    Why would it not be 100% arecoline, when evaluating the cytotoxic properties of arecoline?

    Once again des.... these abstracts are available to the public. The full versions are not.

    Should we overlook what is stated in print.... just because the purity was not indicated?
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    Originally Posted by deserusan View Post
    What was the standardization and was this pure arecoline?

    Pure arecoline is 100% arecoline with no impurities. Is that what they were using?
    chemical grade / pure arecoline.


    from the methods of study 1:

    2. Materials and methods
    All tissue culture biologicals were obtained from Gibco Laboratories (Life technologies, Grand Island, NY, USA). Arecoline, -buthionine-S,R-sulfoximine (BSO), and N-acetyl-cysteine (NAC) were obtained from Sigma Chemical Co. (St. Louis, MO, USA). Fresh AN was purchased from a local market in Taipei. The preparation of ANE was the same as previously described [3].

    In the second study, chemical grade, pure Arecolin was used as well (and purchased from Sigma):

    Materials—Dulbecco's modified Eagle's medium (DMEM), fetal calf serum, penicillin/streptomycin, keratinocyte growth medium (KGM-SFM), pituitary gland extract, and epidermal growth factors etc. were from Invitrogen Life Technologies, Inc. ELISA kits for IL-6 measurement were from BIOSOURCE (BIOSOURCE International, Inc.). Arecoline, 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT), calfskin type I collagen and bovine plasma fibronectin were obtained from Sigma.
    When you go to Sigma you'll get redirected to Sigma Aldrich. They sell Arecoline hydrobromide with a purity of >99%. I guess that this is exactely the Arecolin that has been used in both studies.

    http://www.sigmaaldrich.com/catalog/...ty/FLUKA;10980
    Last edited by Dr.P; 01-03-2008 at 03:58 AM.
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    Originally Posted by deserusan View Post
    Arecoline is perfectly safe.
    Nope
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