MMDA (drug)

MMDA
Clinical data
Routes of; administration	Oral, Insufflation, Rectal
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name 1-(7-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine;
CAS Number	13674-05-0;
PubChem CID	26175;
ChemSpider	24386;
UNII	RG7FY73ZAA;
KEGG	C22812 ;
CompTox Dashboard (EPA)	DTXSID50860757 ;
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O1c2cc(cc(OC)c2OC1)CC(N)C;

MMDA (3-methoxy-4,5-methylenedioxyamphetamine; 5-methoxy-MDA) is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA.

MMDA was described by Alexander Shulgin in his book PiHKAL. Shulgin lists the dosage range of MMDA as 100–250 mg. The first effects appear within 30–60 minutes following oral administration. MMDA produces euphoria and loving warmth, and attenuates feelings such as anxiety and loneliness. MMDA also produces closed eye visuals, a state of drowsiness, muscle relaxation, and time distortion. Side effects include moderate mydriasis, dizziness, sensations of heat or cold, and trembling. The imagery is generally realistic, and often related to everyday perception of people, landscapes, or objects. The effects of MMDA usually reach a peak during the first hour following the initial effects, and begin to wane during the second hour, and usually completely disappear by the end of the fifth hour.

Psychotherapeutic actions

In his 1973 book, The Healing Journey, Claudio Naranjo explored the psychotherapeutic potential of MMDA. Like MDA, he found that MMDA facilitates communication and suggested it has potential applications in psychotherapy. Worldwide as of 2005^[update], MMDA has not been approved for any human applications.

Pharmacology

MMDA has been shown to act as a non-neurotoxic serotonin releasing agent with no effects on dopamine release and probably norepinephrine release as well,^[2] and as a 5-HT_2A receptor agonist.^[3] The latter property is responsible for its psychedelic effects, whereas the former mediates its mood-lifting and empathogenic effects.

Legal Status

United States

MMDA is classified as a Schedule 1 substance in the United States, and is similarly controlled in other parts of the world. MMDA remains illegal, however it is classified differently than the illegality of MDMA.^{[clarification needed]}

Internationally, MMDA is a Schedule I drug under the Convention on Psychotropic Substances.^[4]

Australia

MMDA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[5] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.^[5]

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology Biochemistry and Behavior. 38 (3): 505–12. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. S2CID 2740262.
^ Zhang Z, An L, Hu W, Xiang Y (April 2007). "3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach". Journal of Computer-aided Molecular Design. 21 (4): 145–53. Bibcode:2007JCAMD..21..145Z. doi:10.1007/s10822-006-9090-y. PMID 17203365. S2CID 25343432.
^ "Archived copy" (PDF). Archived from the original (PDF) on 2005-12-05. Retrieved 2005-11-19.{{cite web}}: CS1 maint: archived copy as title (link)
^ ^a ^b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

External links

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[pmid1829838-2] McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology Biochemistry and Behavior. 38 (3): 505–12. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. S2CID 2740262.

[pmid17203365-3] Zhang Z, An L, Hu W, Xiang Y (April 2007). "3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach". Journal of Computer-aided Molecular Design. 21 (4): 145–53. Bibcode:2007JCAMD..21..145Z. doi:10.1007/s10822-006-9090-y. PMID 17203365. S2CID 25343432.

[4] "Archived copy" (PDF). Archived from the original (PDF) on 2005-12-05. Retrieved 2005-11-19.{{cite web}}: CS1 maint: archived copy as title (link)

[Poisons_Standard-5] Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

[1]

[2]

[3]

[4]

[5]