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  1. #1
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    A detailed overview of N-Methyltyramine

    N-Methyltyramine (4-Hydroxy-N-methylphenethylamine)



    Background

    N-Methyltyramine is the methylated version of L-Tyramine (through the addition of a methyl group at the N terminal), a naturally occurring monoamine compound that acts as a catecholamine releasing agent. N-Methyltyramine can be found in nature from plants such as barley and Citrus aurantium, the latter being commonly used for Synephrine content (N-Methyltyramine is converted to Synephrine by Dopamine β -hydroxylase). Unlike Synephrine, N-Methyltyramine has not been observed to display any lipolytic activity, due to the lack of a beta-hydroxyl or a beta-ketone. It’s mechanisms of action imply that it acts as a peripheral sympathomimetic compound. NMT is similar to Synephrine and Hordenine, with the addition of a hydroxyl group at β distinguishing Synephrine from NMT, and substitution of a dimethyl group at the N terminal resulting in Hordenine.

    In general, when dealing with sympathomimetic compounds, a primary or secondary aliphatic amine separated by 2 carbons from a substituted benzene ring is minimally required for high agonist activity. Along with possessing this characteristic common to adrenergic agents, the presence of a hydroxyl group in the benzene ring at the 4th position shows that N-Methyltyramine has excellent alpha and beta activity adrenergic receptor activity.

    Pharmacokinetics

    -39% bioavailability through p.o use.

    -90% of orally ingested NMT is absorbed in the small intestine, particularly in the lower jejunum and the ileum.

    -NMT is metabolized in the liver, but not in the small-intestinal mucosa.

    -Hepatic intrinsic clearance value is 2 liters an hour.

    -The plasma concentration time curve and bioavailability of NMT after oral ingestion were well predicted by the GI transit absorption model with the hepatic first-pass metabolism process.

    Actions

    N-Methyltyramine is known to possess β2 adrenergic receptor activity, to increase plasma and myocardial cGMP and cAMP levels, has been observed to increase renal and cerebral vascular resistance, and lacks a beta-hydroxyl or a beta-ketone group, implying it is an indirect acting amine that releases cytoplasmic norepinephrine from sympathetic nerve endings, similar to tyramine. Vasoconstriction during exercise due to the use of NMT is not likely because during exercise, the α1-adrenergic receptors activated by the norepinephrine released by NMT can be selectively blocked by sympathetic nervous activity, allowing the β2-adrenergic receptors to dominate. While it may appear to have β1-adrenergic activity, there is no observed action on amylase activity after administration of N-Methyltyramine.

    N-Methyltyramine most importantly has the properties of an α2-adrenoceptor antagonist, albeit a weak one. α2 blockers significantly increase adrenergic, dopaminergic and serotonergic neurotransmitters, increase insulin secretion and decrease blood sugar levels. The usage of N-Methyltyramine also leads to an increase in blood pressure, relaxation of the ileum, an increase in force of the right atrium due to norepinephrine release, and an increase in rate of contraction in right atrium due to norepinephrine release.

    N-Methyltyramine has also been found to be a constituent of beer. When tested, N-Methyltyramine was found to stimulate pancreatic secretion via the cholinergic gastro-pancreatic reflex, meaning the stimulation of pancreatic secretion observed after drinking is likely due to N-Methyltyramine, along with obviously ethanol. Although gastrin production may of concern to those looking to use N-Methyltyramine, it is likely only to be an issue for those who are predisposed to illnesses such as hypercalcaemia, and the dosage required of NMT for this likely exceeds doses that will be utilized for p.o use. As always, consumers should check with their physician before the use of any supplement, so if there is any concern, please check with your physician before using NMT.

    Summary

    N-Methyltyramine is the methylated version of L-Tyramine, a naturally occurring monoamine compound that acts as a catecholamine releasing agent. It is known to:

    • Significantly increase adrenergic, dopaminergic and serotonergic neurotransmitters by acting as an indirect sympathomimetic amine.

    • Increases insulin secretion and decreases blood sugar levels.

    • Increase plasma and myocardial cGMP and cAMP levels.

    -----------------------------------------------------------------------------------------------------

    On whether I'd use it or not, I would. Some people I know have tried it and said it was quite excellent, and I look forward to trying it myself. Also, I didn't include citations because I was lazy when I wrote this (wasn't going to post it up on here but figured why not), but it wouldn't be hard to find the source if you were particularly interested in something.
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  2. #2
    Hates most people TMac26's Avatar
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    Thumbs up

    Great right up broseph.
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    Disclaimer: The above post is my personal opinion and does not represent the official position of any company or entity.
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  3. #3
    interact with me PinchTheBear's Avatar
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    Originally Posted by Synapsin View Post
    Unlike Synephrine, N-Methyltyramine has not been observed to display any lipolytic activity, due to the lack of a beta-hydroxyl or a beta-ketone.
    Where'd you read that a carbonyl group at the beta carbon influences direct beta adrenergic activity? An upward (i.e. 1R) oriented OH is necessary: in TM3, asp-113 accepts an h-bond from the beta-OH and forms salt bridge with protonated amine of the agonist. If you find the source email me it.

    http://www.pnas.org/content/101/9/2736.full
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  4. #4
    Veritas. Aequitas. neuron's Avatar
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    Great article synapsin.

    From the chinese study on myocardial function, the authors concluded that it is indeed a releasing agent like tyramine. I didn't include it in the OP because I couldn't find a full-text.

    Nevertheless, a releasing agent is a poor choice for a replacement for 1,3-DMAA, although the supp world is pretty limited for alternatives.
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    Veritas. Aequitas. neuron's Avatar
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    Originally Posted by Synapsin View Post
    N-Methyltyramine is known to possess β2 adrenergic receptor activity
    NMT's direct activity is antagonistic to the adrenergic receptor, so this is slightly misleading.
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  6. #6
    Veritas. Aequitas. neuron's Avatar
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    Originally Posted by PinchTheBear View Post
    Where'd you read that a carbonyl group at the beta carbon influences direct beta adrenergic activity? An upward (i.e. 1R) oriented OH is necessary: in TM3, asp-113 accepts an h-bond from the beta-OH and forms salt bridge with protonated amine of the agonist. If you find the source email me it.

    http://www.pnas.org/content/101/9/2736.full
    If I recall correctly, a beta-ketone will also activate the beta receptor (i.e. cathinone).
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  7. #7
    Primum non nocere Synapsin's Avatar
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    Originally Posted by PinchTheBear View Post
    Where'd you read that a carbonyl group at the beta carbon influences direct beta adrenergic activity? An upward (i.e. 1R) oriented OH is necessary: in TM3, asp-113 accepts an h-bond from the beta-OH and forms salt bridge with protonated amine of the agonist. If you find the source email me it.

    http://www.pnas.org/content/101/9/2736.full
    Originally Posted by neuron View Post
    If I recall correctly, a beta-ketone will also activate the beta receptor (i.e. cathinone).
    Yep!

    http://www.ncbi.nlm.nih.gov/pubmed/2927251

    Originally Posted by neuron View Post
    Great article synapsin.

    From the chinese study on myocardial function, the authors concluded that it is indeed a releasing agent like tyramine. I didn't include it in the OP because I couldn't find a full-text.

    Nevertheless, a releasing agent is a poor choice for a replacement for 1,3-DMAA, although the supp world is pretty limited for alternatives.
    Thanks, I appreciate it. Also, agreed on the second statement, but like you said, the supplement world is limited and I personally enjoy 1,3 so I have no problems trying NMT.

    Originally Posted by neuron View Post
    NMT's direct activity is antagonistic to the adrenergic receptor, so this is slightly misleading.
    Indeed, I was considering the fact that it increased cAMP levels and cardiac output, but you're right, it more closely resembles alpha 2 antagonistic behaviour more than beta 2 agonist behaviour, lawl, confirmation bias.
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    the read was enjoyed in a dejavu-esque fashion
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    After reading stuff like this I realize I'm just scratching the surface. I'll go back to designing space ships for now.
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    Good research summary here: http://supplementruth.com/supplement...rus-aurantium/

    Its not completely positive but more because the research has not really been done to give it the all clear. Any personal experiences of taking this esp. with regards to actually 'feeling' it in an ephedrine like manner?
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  11. #11
    nom nom nom deserusan's Avatar
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    Nice article. I have tried NMT in varying doses and do like it albeit it works best in synergy with other compounds. I'm not sure if you guys know it or not, but it has been out for awhile in a product called MethyBurn.
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  12. #12
    Still talking to the CEO ERGOGENIX's Avatar
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    Nice article Syn.
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    wow interesting thanks for sharin
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    interact with me PinchTheBear's Avatar
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    Syn, think you'd be able to approximate a ClogP for NMT?
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    Great write-up, M. Dang, I wish I knew half as much as you did about supp. ingredients.
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    Primum non nocere Synapsin's Avatar
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    Originally Posted by deserusan View Post
    Nice article. I have tried NMT in varying doses and do like it albeit it works best in synergy with other compounds. I'm not sure if you guys know it or not, but it has been out for awhile in a product called MethyBurn.
    Thanks, and I didn't know that actually, pretty cool. As for synergy, yeah, I'd use NMT in a product that has caffeine, probably wouldn't bother with it alone.

    Originally Posted by ERGOGENIX View Post
    Nice article Syn.
    Thanks J!

    Originally Posted by SynchroGym
    wow interesting thanks for sharin
    Thanks man.

    Originally Posted by PinchTheBear View Post
    Syn, think you'd be able to approximate a ClogP for NMT?
    I see different values around but safe to say around ~1.3.

    Originally Posted by drooks10 View Post
    Great write-up, M. Dang, I wish I knew half as much as you did about supp. ingredients.
    Thanks D, I hope all is well with the wife and kids, happy fathers day (you too as well James and Dan).
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    Originally Posted by deserusan View Post
    Nice article. I have tried NMT in varying doses and do like it albeit it works best in synergy with other compounds. I'm not sure if you guys know it or not, but it has been out for awhile in a product called MethyBurn.
    I did enjoy my run of Methylburn when I used it.

    Even with the yohimbine it was never overpowering.
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    Questions regarding form

    I have been a longtime purchaser of the 1,3 products. I see that the Ergogenix product write-ups center on N-methyltyramine, but their products contain N-methyltyramine HCI. Are not those two different chemicals? Would they both have the same effect?
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    interact with me PinchTheBear's Avatar
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    Originally Posted by prokarter View Post
    I have been a longtime purchaser of the 1,3 products. I see that the Ergogenix product write-ups center on N-methyltyramine, but their products contain N-methyltyramine HCI. Are not those two different chemicals? Would they both have the same effect?
    N-methyltyramine HCl denotes a hydrochloride salt of NMT. The HCl is there for kinetic reasons and has no pharmacological effect on the associated base (NMT).
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    Originally Posted by PinchTheBear View Post
    N-methyltyramine HCl denotes a hydrochloride salt of NMT. The HCl is there for kinetic reasons and has no pharmacological effect on the associated base (NMT).
    Thanks.
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  21. #21
    One Day at a Time Bane81's Avatar
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    NMT wouldn't have any negative effects on a drug test would it?
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    Hates most people TMac26's Avatar
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    Originally Posted by Bane81 View Post
    NMT wouldn't have any negative effects on a drug test would it?

    You're good. I've been tested personally while on NMT
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    so what ended up being the consensus opinion on this purported wonder stimulant?
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    just curious with all the ampehtamine talk going on in here, would this or any other PHEN's such as in conquer or core fury show up on a drug test as an ampehtamine?
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    Originally Posted by jaredmus View Post
    just curious with all the ampehtamine talk going on in here, would this or any other PHEN's such as in conquer or core fury show up on a drug test as an ampehtamine?
    As in what?
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  26. #26
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    Originally Posted by Mr.Cooper69 View Post
    As in what?
    i mean as in the whole Phenyl ingredients and NMT supplements like that will they cause you to fail a drug test and show up as an ampethamine?
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