Para-Methoxyamphetamine

*para*-Methoxyamphetamine
Clinical data
Trade names	Dr.Death
Routes of; administration	Oral
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; In general illegal unless that was for medical, therapeutic or scientific use.;
Identifiers
	IUPAC name 1-(4-methoxyphenyl)propan-2-amine;
CAS Number	64-13-1 ;
PubChem CID	31721;
DrugBank	DB01472 ;
ChemSpider	29417 ;
UNII	OVB8F8P39Q;
KEGG	C22811 ;
ChEMBL	ChEMBL278663 ;
CompTox Dashboard (EPA)	DTXSID7040578 ;
ECHA InfoCard	100.000.525
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=CC=C1CC(C)N)OC;
	InChI InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3 ; Key:NEGYEDYHPHMHGK-UHFFFAOYSA-N ;
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para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects.^[2]^[3]^[4] Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects,^[5] and behaves more like an antidepressant in comparison,^[6] though it does have some psychedelic properties.^[7]^[8]

PMA has been found in tablets touted as MDMA (ecstasy)^[9]^[10]^[11]^[12] although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the flavor compound of anise and fennel, mainly because the starting material for MDMA, safrole, has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole as an alternative.^[13]

^ 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.
^ Drug Enforcement Administration October 2000. The Hallucinogen PMA: Dancing With Death
^ Shulgin AT, Shulgin A (1991). "#97 4-MA". Pihkal: A Chemical Love Story. Transform Press. ISBN 978-0-9630096-0-9.
^ Karlis S (7 April 2008). "Warning of possible shift to killer drug". Sydney Morning Herald. Fairfax. Retrieved 2008-06-29.
^ Corrigall WA, Robertson JM, Coen KM, Lodge BA (January 1992). "The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine". Pharmacology, Biochemistry, and Behavior. 41 (1): 165–169. CiteSeerX 10.1.1.670.6929. doi:10.1016/0091-3057(92)90077-S. PMID 1539067. S2CID 30080516.
^ Preve M, Suardi NE, Godio M, Traber R, Colombo RA (April 2017). "Paramethoxymethamphetamine (Mitsubishi turbo) abuse: Case report and literature review". European Psychiatry. 41 (S1): s875. doi:10.1016/j.eurpsy.2017.01.1762. S2CID 148876431.
^ Hegadoren KM, Martin-Iverson MT, Baker GB (April 1995). "Comparative behavioural and neurochemical studies with a psychomotor stimulant, an hallucinogen and 3,4-methylenedioxy analogues of amphetamine". Psychopharmacology. 118 (3): 295–304. doi:10.1007/BF02245958. PMID 7617822. S2CID 30756295.
^ Winter JC (February 1984). "The stimulus properties of para-methoxyamphetamine: a nonessential serotonergic component". Pharmacology, Biochemistry, and Behavior. 20 (2): 201–203. doi:10.1016/0091-3057(84)90242-9. PMID 6546992. S2CID 9673028.
^ "EcstasyData.org: Results : Lab Test Results for Recreational Drugs". www.ecstasydata.org.
^ Davies C (10 July 2013). "Warning over fake ecstasy tablets after seven people die in Scotland". The Guardian. Retrieved 10 July 2013.
^ Barrell R (2 January 2015). "Four Dead Amid Fears Of Dodgy Batch Of 'Superman' Ecstasy Hitting The UK". HuffPost UK.
^ Byard RW, Gilbert J, James R, Lokan RJ (September 1998). "Amphetamine derivative fatalities in South Australia--is "Ecstasy" the culprit?". The American Journal of Forensic Medicine and Pathology. 19 (3): 261–265. doi:10.1097/00000433-199809000-00013. PMID 9760094.
^ Waumans D, Bruneel N, Tytgat J (April 2003). "Anise oil as para-methoxyamphetamine (PMA) precursor". Forensic Science International. 133 (1–2): 159–170. doi:10.1016/S0379-0738(03)00063-X. PMID 12742705.

[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.

[2] Drug Enforcement Administration October 2000. The Hallucinogen PMA: Dancing With Death

[Alexander_&_Ann_Shulgin,_PiHKAL_#97-3] Shulgin AT, Shulgin A (1991). "#97 4-MA". Pihkal: A Chemical Love Story. Transform Press. ISBN 978-0-9630096-0-9.

[salna-4] Karlis S (7 April 2008). "Warning of possible shift to killer drug". Sydney Morning Herald. Fairfax. Retrieved 2008-06-29.

[pmid1539067-5] Corrigall WA, Robertson JM, Coen KM, Lodge BA (January 1992). "The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine". Pharmacology, Biochemistry, and Behavior. 41 (1): 165–169. CiteSeerX 10.1.1.670.6929. doi:10.1016/0091-3057(92)90077-S. PMID 1539067. S2CID 30080516.

[6] Preve M, Suardi NE, Godio M, Traber R, Colombo RA (April 2017). "Paramethoxymethamphetamine (Mitsubishi turbo) abuse: Case report and literature review". European Psychiatry. 41 (S1): s875. doi:10.1016/j.eurpsy.2017.01.1762. S2CID 148876431.

[pmid7617822-7] Hegadoren KM, Martin-Iverson MT, Baker GB (April 1995). "Comparative behavioural and neurochemical studies with a psychomotor stimulant, an hallucinogen and 3,4-methylenedioxy analogues of amphetamine". Psychopharmacology. 118 (3): 295–304. doi:10.1007/BF02245958. PMID 7617822. S2CID 30756295.

[pmid6546992-8] Winter JC (February 1984). "The stimulus properties of para-methoxyamphetamine: a nonessential serotonergic component". Pharmacology, Biochemistry, and Behavior. 20 (2): 201–203. doi:10.1016/0091-3057(84)90242-9. PMID 6546992. S2CID 9673028.

[ecstasydata-9] "EcstasyData.org: Results : Lab Test Results for Recreational Drugs". www.ecstasydata.org.

[fake-ecstasy-warning-die-scotland-10] Davies C (10 July 2013). "Warning over fake ecstasy tablets after seven people die in Scotland". The Guardian. Retrieved 10 July 2013.

[Barrell2015-11] Barrell R (2 January 2015). "Four Dead Amid Fears Of Dodgy Batch Of 'Superman' Ecstasy Hitting The UK". HuffPost UK.

[pmid9760094-12] Byard RW, Gilbert J, James R, Lokan RJ (September 1998). "Amphetamine derivative fatalities in South Australia--is "Ecstasy" the culprit?". The American Journal of Forensic Medicine and Pathology. 19 (3): 261–265. doi:10.1097/00000433-199809000-00013. PMID 9760094.

[13] Waumans D, Bruneel N, Tytgat J (April 2003). "Anise oil as para-methoxyamphetamine (PMA) precursor". Forensic Science International. 133 (1–2): 159–170. doi:10.1016/S0379-0738(03)00063-X. PMID 12742705.

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Clinical data


Trade names	Dr.Death
Routes of administration	Oral
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)^[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I UN: Psychotropic Schedule I In general illegal unless that was for medical, therapeutic or scientific use.
Identifiers
IUPAC name 1-(4-methoxyphenyl)propan-2-amine
CAS Number	64-13-1^Y
PubChem CID	31721
DrugBank	DB01472^Y
ChemSpider	29417^Y
UNII	OVB8F8P39Q
KEGG	C22811^Y
ChEMBL	ChEMBL278663^Y
CompTox Dashboard (EPA)	DTXSID7040578
ECHA InfoCard	100.000.525
Chemical and physical data
Formula	C₁₀H₁₅NO
Molar mass	165.236 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1CC(C)N)OC
InChI InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3^Y Key:NEGYEDYHPHMHGK-UHFFFAOYSA-N^Y
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