2C-MMDA-3a
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| Other names | 2C-3a; 2-Methoxy-3,4-methylenedioxyphenethylamine; 2-Methoxy-MDPEA; 2-MeO-MDPEA; 2-Methoxy-3,4-MDPEA; 2-MeO-3,4-MDPEA; MMDPEA-3a |
| Routes of administration | Oral[1] |
| Drug class | Psychoactive drug |
| ATC code |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
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| Chemical and physical data | |
| Formula | C10H13NO3 |
| Molar mass | 195.218 g·mol−1 |
| 3D model (JSmol) | |
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2C-MMDA-3a, also known as 2C-3a, MMDPEA-3a, or 2-methoxy-3,4-methylenedioxyphenethylamine (2-methoxy-MDPEA), is a psychoactive drug of the phenethylamine and MDxx families related to 3,4-methylenedioxyphenethylamine (MDPEA).[1][2] It is the phenethylamine (2C) analogue of MMDA-3a and the 2-methoxy derivative of MDPEA.[1][2] According to Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved), 2C-MMDA-3a has a dose range of 40 to 120 mg orally with marginal effects.[1] At 40 mg, there was perhaps the hint of a psychic energizer (antidepressant); at 65 mg, there was pleasant mood elevation; and at 80 and 120 mg, there was brief parasthesia.[1] Shulgin has noted the modest change in effects with the drug over a three-fold dose range and has wondered whether it might be useful as an antidepressant or might be a serotonin reuptake inhibitor.[1] The chemical synthesis of 2C-MMDA-3a has been described.[1][2] It was first described in the scientific literature by Shulgin and colleagues by 1969.[3]
See also
[edit]- Substituted methylenedioxyphenethylamine
- Substituted methoxyphenethylamine
- Methoxymethylenedioxyphenethylamine
- Lophophine (2C-MMDA-1 or MMDPEA-1)
- 2C-MMDA-2
- 2C2-NBOMe (2C-MMDA-2-NBOMe)
References
[edit]- 1 2 3 4 5 6 7 8 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal134.shtml "And, as with MMDA-2, both the 2-carbon "phenethylamine" analogue and the 4-carbon RARIADNES analogue of MMDA-3a have been made. The phenethylamine analog was prepared by the condensation of 7.6 g of the above benzaldehyde with nitromethane (in acetic acid with ammonium acetate catalyst, giving 5.4 g of the nitrostyrene with a mp of 115.5-116.5 °C from methanol) followed by lithium aluminum hydride reduction (in ether). The product, 2-methoxy-3,4-methylenedioxyphenethylamine hydrochloride (2C-3a) melted at 143-145 °C. A series of subjective evaluations were made, and there are reports of marginal effects in the 40 to 120 milligram range. At 40 milligrams, perhaps the hint of a psychic energizer; at 65 milligrams, there was a pleasant mood elevation; at 80 milligrams, there was a brief paresthetic twinge noted at about the hour and a half point, and at 120 milligrams, about the same at one hour, and then nothing. The fact that there can be such a modest change of effect over a three-fold range of dosage suggests that this compound might have some merit as an anti-depressant. It would be interesting to know if it blocks serotonin reuptake!"
- 1 2 3 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ↑ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297. Archived from the original on 2025-07-12.
External links
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