2C-MMDA-3a

Last updated

2C-MMDA-3a
2C-MMDA-3a.svg
Clinical data
Other names2C-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
  • None
Pharmacokinetic data
Duration of action Unknown [1]
Identifiers
  • 2-(4-methoxy-1,3-benzodioxol-5-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C10H13NO3
Molar mass 195.218 g·mol−1
3D model (JSmol)
  • COC1=C(C=CC2=C1OCO2)CCN
  • 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]

Contents

See also

References

  1. 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!"
  2. 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.
  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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