2C-MMDA-3a

2C-MMDA-3a
Clinical data
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
Drug class	Psychoactive drug
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 2-(4-methoxy-1,3-benzodioxol-5-yl)ethanamine;
CAS Number	2220-19-1;
PubChem CID	11127161;
ChemSpider	9302281;
ChEMBL	ChEMBL1196834;
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C=CC2=C1OCO2)CCN;
	InChI InChI=1S/C10H13NO3/c1-12-9-7(4-5-11)2-3-8-10(9)14-6-13-8/h2-3H,4-6,11H2,1H3; Key:AXEJSBWWIHAWJM-UHFFFAOYSA-N;

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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h 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!"
^ ^a ^b ^c 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

2C-3a (2C-MMDA-3a) - Isomer Design

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[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h 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!"

[Shulgin_2011-2] 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_1969-3] 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.

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[3]

See also

References

External links