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All 5 posts Subject: MMDA Please login to post Down

pablos
(Newbee)
11-07-04 19:15
No 540230
      MMDA

I try to produce Myristicine aldehyde with the 3base procedure from Bromovanilline, but I got no Nitroethane.
Is the phenyletylamine counterpart of 3-METHOXY-4,5-METHYLENEDIOXYAMPHETAMINE active?

hypo
(Balanced Ego)
11-07-04 19:21
No 540231
      >200mg

http://www.erowid.org/library/books_online/pihkal/pihkal095.shtml

HÎ¨=EÎ¨

phenethyl_man
(Hive Bee)
11-08-04 06:36
No 540376
      2-methoxy-4,5-methylenedioxyphenethylamine..

I seriously doubt it shows much activity until the 400mg range.   Even MMDA is not very potent and requires around 200mg for an enjoyable experience. For comparison, the trimethoxyphenethylamine that shares this substitution pattern, Mescaline, is active around 350-400mg. The corresponding amphetamine, TMA, is active around 150mg. I would expect Lophophine to be even less potent then Mescaline. Shulgin was only interested in this compound because there is an tetrahydroisoquinoline alkaloid in peyote, Lophophorine, that would result from cyclization of this phenethylamine.

Perhaps the 2-methoxy-4,5-methylenedioxyphenethylamine would be more interesting since MMDA-2 is the most potent of this series. I've been considering exploring this one since the aldehyde could be obtained through bromination of benzodioxole, and then swapping the halogen w/a methoxyl, followed by formylation. Or, from vanillin, you could produce piperonal and react this with H2O2 in methanol. Or do a baeyer-villiger w/HCO3H to the formate ester, followed by hydrolysis should get you to sesamol. Then ortho-formylate sesamol and methylate and you would have the necessary aldehyde..

or perhaps you should just wait till you can find some EtNO2 since you have come this far already and lophophine is prob not worth it..

- phenethylman -

Fastandbulbous
(Hive Bee)
11-12-04 03:53
No 541152
User Picture       Hmmm

phenethyl_man; I don't want to be a nay sayer, but I think that the 2,4,5-substitution pattern for methoxy/methylenedioxy phenethylamines is subject to fairly quick metabolism by MAO. 2,4,5-trimethoxyphenethylamine doesnt even get a look in on the activity stakes if you have a look at PIHKAL.

I think the two adjacent oxygen atoms of the 2,4,5 substitution pattern (as in catecholamines) makes them a good substrate for MAO. With the 2,4,5 pattern, the 4 substitution needs to be something other than oxygen to be resistant to metabolism by MAO.

I'm sure I've seen other studies with 3-methoxy-4,5-methylenedioxyPEA that stated that it had activity at around the 200mg mark that was more of an empathy enhancer. If you upped the dose to that similar to mescaline (350-400mg), then it produced a full on psychedelic experience

That is right, the Mascara Snake: Fast and bulbous

phenethyl_man
(Hive Bee)
11-12-04 05:10
No 541161
      I agree with you for the most part, however,...

I agree with you for the most part, however, even though both 2,4,5-trimethoxy-PEA and 2-methoxy-4,5-methylenedioxy-PEA both have vicinal oxygen atoms, this does not mean they will share the same metabolic fate.

Think about 2,3,4-trimethoxyamphetamine, the only TMA compound which is considered to be inactive. However, the same exact substitution pattern is shared by MMDA-3a and MMDA-3b which are both active at less than 100mg.

This makes me think that perhaps the conformationally restricted methylenedioxy ring is more resistant than the corresponding free methoxy derivatives. Consider Nichols' work with benzofuran derivatives based on the DOx-series which has led to the discovery of some of the most potent phenethylamines known.

Of course this discussion is purely theoretical, and the effects a compound will exert in vivo is nearly impossible to predict. Certainly the unique action of MDMA could never have been expected based on the results of N-methylation of the other psychedelic amphetamines.

It also has as much, if not more, to do with the compound's interaction with 5-HT2x receptors than it's susceptibility to metabolism. Besides, MAO can be taken care of w/a MAO inhibitor (orally) or simply administering the compound thru a different route (i.e. smoking the freebase.), this requirement hasn't diminished DMT's popularity that much is for sure.

I just feel this would be an interesting compound to explore, considering no one has (to my knowledge) done so.

- phenethylman -

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		pablos (Newbee) 11-07-04 19:15 No 540230				MMDA
						I try to produce Myristicine aldehyde with the 3base procedure from Bromovanilline, but I got no Nitroethane. Is the phenyletylamine counterpart of 3-METHOXY-4,5-METHYLENEDIOXYAMPHETAMINE active?



		hypo (Balanced Ego) 11-07-04 19:21 No 540231				>200mg
						http://www.erowid.org/library/books_online/pihkal/pihkal095.shtml HÎ¨=EÎ¨



		phenethyl_man (Hive Bee) 11-08-04 06:36 No 540376				2-methoxy-4,5-methylenedioxyphenethylamine..
						I seriously doubt it shows much activity until the 400mg range. Even MMDA is not very potent and requires around 200mg for an enjoyable experience. For comparison, the trimethoxyphenethylamine that shares this substitution pattern, Mescaline, is active around 350-400mg. The corresponding amphetamine, TMA, is active around 150mg. I would expect Lophophine to be even less potent then Mescaline. Shulgin was only interested in this compound because there is an tetrahydroisoquinoline alkaloid in peyote, Lophophorine, that would result from cyclization of this phenethylamine. Perhaps the 2-methoxy-4,5-methylenedioxyphenethylamine would be more interesting since MMDA-2 is the most potent of this series. I've been considering exploring this one since the aldehyde could be obtained through bromination of benzodioxole, and then swapping the halogen w/a methoxyl, followed by formylation. Or, from vanillin, you could produce piperonal and react this with H2O2 in methanol. Or do a baeyer-villiger w/HCO3H to the formate ester, followed by hydrolysis should get you to sesamol. Then ortho-formylate sesamol and methylate and you would have the necessary aldehyde.. or perhaps you should just wait till you can find some EtNO2 since you have come this far already and lophophine is prob not worth it.. - phenethylman -



		Fastandbulbous (Hive Bee) 11-12-04 03:53 No 541152				Hmmm
						phenethyl_man; I don't want to be a nay sayer, but I think that the 2,4,5-substitution pattern for methoxy/methylenedioxy phenethylamines is subject to fairly quick metabolism by MAO. 2,4,5-trimethoxyphenethylamine doesnt even get a look in on the activity stakes if you have a look at PIHKAL. I think the two adjacent oxygen atoms of the 2,4,5 substitution pattern (as in catecholamines) makes them a good substrate for MAO. With the 2,4,5 pattern, the 4 substitution needs to be something other than oxygen to be resistant to metabolism by MAO. I'm sure I've seen other studies with 3-methoxy-4,5-methylenedioxyPEA that stated that it had activity at around the 200mg mark that was more of an empathy enhancer. If you upped the dose to that similar to mescaline (350-400mg), then it produced a full on psychedelic experience That is right, the Mascara Snake: Fast and bulbous



		phenethyl_man (Hive Bee) 11-12-04 05:10 No 541161				I agree with you for the most part, however,...
						I agree with you for the most part, however, even though both 2,4,5-trimethoxy-PEA and 2-methoxy-4,5-methylenedioxy-PEA both have vicinal oxygen atoms, this does not mean they will share the same metabolic fate. Think about 2,3,4-trimethoxyamphetamine, the only TMA compound which is considered to be inactive. However, the same exact substitution pattern is shared by MMDA-3a and MMDA-3b which are both active at less than 100mg. This makes me think that perhaps the conformationally restricted methylenedioxy ring is more resistant than the corresponding free methoxy derivatives. Consider Nichols' work with benzofuran derivatives based on the DOx-series which has led to the discovery of some of the most potent phenethylamines known. Of course this discussion is purely theoretical, and the effects a compound will exert in vivo is nearly impossible to predict. Certainly the unique action of MDMA could never have been expected based on the results of N-methylation of the other psychedelic amphetamines. It also has as much, if not more, to do with the compound's interaction with 5-HT2x receptors than it's susceptibility to metabolism. Besides, MAO can be taken care of w/a MAO inhibitor (orally) or simply administering the compound thru a different route (i.e. smoking the freebase.), this requirement hasn't diminished DMT's popularity that much is for sure. I just feel this would be an interesting compound to explore, considering no one has (to my knowledge) done so. - phenethylman -

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