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MMA - 3-MeO-4-Me-Amphetamine

Holy_cow

Holy_cow

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Nov 29, 2007
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Is there anything known about this compound except the short note in Shulgin's book and the Nichols paper showing that it substitutes (in rats) for MDMA? Anyone tried the stuff?
 
I suspect that plain(?) 3 methoxy amphetamine will work like MDMA...
 
^ Agreed, is the 4-methoxy compound known? Both would be very interesting to taste and would likely sub for MDMA.
 
Yeah, no, not PMA, but 3,4-methoxy... should be a lot more careful.

I wouldn't touch that shit with a 10' pole.
 
I think it's fine if you're careful with the dose. It seems to have quite a steep dose response curve, at about 40 mg it was quite a nice stimulant for a few hours. At about 60 mg though it felt like coming up on two pills at once for a while, was pretty intense, i wouldn't want to take a higher dose.
 
Mma

PiHKAL, page 770 (under the MEPEA #123 entry discussion):

"Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semitransparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug. This was shown to contain an analogue of DOM called MMA, or 3-methoxy-4-methylamphetamine. The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40 to 60 millligrams. The compound can apparently be quite dysphoric, and long lived."--Alexander Shulgin.

Makes me wonder about 4-ethyl-3-methoxyamphetamine, EMA, the 2-des-MeO analogue of DOET.
 
Has anyone got further information on 3 methoxy amphetamine. I keep hearing people saying it's like MDMA but I cannot find any studies.
As for PMA, I have taken it. Unlike MDMA where you go up, hover and come down, it's more like you go from 0 to peak really suddenly, then it wears off (quite quickly). I've never tried PMMA but people tell me it's a little more gentle.
 
haribo1: Serotonin receptor affinities of psychoactive phenalkylamine analogs. Journal of Medicinal Chemistry (1980), 23(3), 294-9. has some (but rather limited) data on different methoxylated phenethylamines including 3-MeO-amphetamine. The following references have some could-be-interesting data in their abstracts, but are (very) hard to get (hence I do not have them).

Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines.
Journal of Pharmacology and Experimental Therapeutics (1976), 197, (2), 272-9

The effects of dl-para-methoxyamphetamine-HCl (dl-PMA) [52740-56-4], dl-meta-methoxyamphetamine-HCl (dl-MMA) [54376-87-3] and dl-ortho-methoxyamphetamine (dl-OMA) [52850-78-9], and d-amphetamine sulfate (d-A) [51-63-8] on the myoclonic twitch activity (MTA) of suprahyoideal muscle in rats and locomotor activity in rats and mice were studied. PMA, MMA and d-A increased the MTA but OMA was ineffective. The increased MTA induced by d-A was not influenced by the blockade of 5-hydroxytryptamine (5-HT) [50-67-9] receptor by methysergide or inhibition of 5-HT synthesis by para-chlorophenylalanine (PCPA) but was reduced by haloperidol which blocked the dopamine [51-61-6] receptor. On the other hand, the increased MTA produced by PMA was not influenced by haloperidol but was reduced by methysergide and PCPA. The increased MTA induced by MMA was not effectively blocked by either PCPA or haloperidol but was blocked by the combination of both PCPA and haloperidol. The results indicate that whereas the increased MTA produced by d-A is not dependent on the availability of 5-HT, PMA exerts its effect by a release of 5-HT and that the MMA effect is due to a release of both 5-HT and dopamine. High doses of PMA and MMA increased the locomotor activity and produced hyperthermia but OMA was inactive. The findings are in agreement with previous biochem. findings that PMA releases 5-HT in brain tissue and suggests that PMA exerts it pharmacol. effects by releasing 5-HT.
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Comparative actions of monomethoxyamphetamines of the release and uptake of biogenic amines in brain tissue.
Journal of Pharmacology and Experimental Therapeutics (1976), 197, (2), 263-71.

P-methoxyamphetamine (PMA), a known hallucinogen, is the most potent of the methoxyamphetamines in disrupting behavior in rats. PMA, unlike d-amphetamine (A), did not induce stereotyped behavior and was less effective than A in stimulation of locomotor d-amphetaminelike effects, and o-methoxyamphetamine (OMA) was devoid of any locomotor stimulation. To investigate the reasons for the different behavioral effects caused by PMA, m-methoxyamphetamine (MMA), OMA, and A, a comparison was made among these drugs on the release and uptake of hydroxytryptamine-3H(5-HT-3H), norepinephrine-3H(NE-3H), and dopamine-3H(DA-3H) by tissue slices of cerebral cortex and corpus striatum of rat brain. The potencies for the increased release of 5-HT-3H in cerebral cortex were PMA > MMA A > OMA, of NE-3H in cortex, A PMA = MMA > OMA, and of DA-3H in corpus striatum, A > MMA > PMA OMA. The potencies for inhibiting the uptake of 5-HT-3H in cerebral cortex and corpus striatum were PMA > MMA > A > OMA, of NE-3H in cortex, A > PMA MMA > OMA, and of DA-3H in corpus striatum, A > MMA > PMA > OMA. D-PMA is equipotent to l-PMA in increasing the release of 5-HT-3H, but is more potent that l-PMA in blocking the uptake of 5-HT-3H. The high potency of PMA in increasing the release and inhibiting the uptake of 5-HT-3H suggests that 5-HT-3H may be involved in the prodn. of hallucinogenic effects of PMA.
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Vasopressor effect of 3-methoxyamphetamine in man.
Adipositas, Kreislauf, Anorektika, [Vortr. Symp.] (1974), Meeting Date 1970, 175-83.

Like other amphetamines, 3-methoxyamphetamine (I) [17862-85-0] had a transient pressor effect on man. The minimal effective dose on oral administration was 25 mg. Differences between that dose and a placebo were significant in young normotensive subjects. The acute response of older patients with chronic hypotension to the same dose was unpredictable. Unlike other amphetamines, this drug did not produce any tachycardia. There was no sustained elevation of blood pressure when the drug was given twice daily for 3 days. The urinary excretion of catechol amines was unchanged.
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Role of biogenic amines in the actions of monomethoxyamphetamines.
Psychopharmacol. Hallucinogens, [Workshop] (1978), Meeting Date 1976, 13-22.

d,l-p-Methoxyamphetamine (I) [23239-32-9] was more effective than d,l-o-methoxyamphetamine [52850-78-9], d,l-m-methoxyamphetamine [17862-91-8], or d-amphetamine [51-64-9] in blocking the uptake or increasing the release of 5-hydroxytryptamine [50-67-9] by brain tissue slices. Amphetamine was more effective than the methoxy analogs in increasing the release or blocking the uptake of dopamine [51-61-6] or norepinephrine [51-41-2]. I was less effective than the m-isomer in affecting the release and uptake of dopamine. The o-isomer was the least effective of all 3 biogenic amines. Amphetamine and the p- and m- (but not the o-) methoxy compds. increased myoclonic twitch activity in rats. In addn., I and m-methoxyamphetamine stimulated locomotor activity, whereas the o-isomer did not. I was 10 times more effective than amphetamine in increasing the release of 5-hydroxytryptamine by the rat brain in vivo. This effect of I did not appear to be due to inhibition of 5-hydroxytryptamine uptake. The neuronal 5-hydroxytryptamine uptake inhibitor chlorimipramine inhibited the effect of I on food-reinforced and locomotor behavior and on myoclonic twitch activity.
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3-methoxy-amp to 3-methoxy-methamp should be quite different, though. The methamp deriv is going to have much stronger activity at SE (assuming it follows a similar pattern)
 
Holy_cow said:
Is there anything known about this compound except the short note in Shulgin's book and the Nichols paper showing that it substitutes (in rats) for MDMA? Anyone tried the stuff?
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Yes.

I am currently on my third trial with MMA (3-Methoxy-4-Methyl-Amphetamine), and it is in every bit the 4x as potent MDxx analogue i was hoping for.
It is not at all dysphoric, like PIHKAL suggests, but very empathic, stimulating, good humored and beautifull 2C-x like visuals at 50 mg.

Although it is a little more long-lived, say up to 12-16 hours depending on dosage, it is manegable.
Actually you get a nice afterglow, instead of a comedown!

This compound is a real treasure if you ask me!

Dex
 
Interesting. Are there also similarities to MDMA in regards to cardiovascular effects and body temp increases ?
 
After looking at the reptake inhibition and neurotransmitter releasing activity of 3-MeO-4-Me-amphetamine (samd Nicols paper that mentions IAP), I'd have thought it would have been rejected because of it's poor activity for dopamine & noradrenaline. Activity re., 5HT simply isn't enough to give the MDMA like euphoria
 
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