Tranylcypromine

Tranylcypromine
	(1S,2R)-(−)-tranylcypromine (top),; (1R,2S)-(+)-tranylcypromine (bottom)
Clinical data
Trade names	Parnate, many generics
Other names	trans-2-phenylcyclopropylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a682088
Pregnancy; category	AU: B2; ;
Routes of; administration	Oral
ATC code	N06AF04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	50%
Metabolism	Liver
Elimination half-life	2.5 hours
Excretion	Urine, Feces
Identifiers
	IUPAC name (±)-trans-2-phenylcyclopropan-1-amine; or; rel-(1R,2S)-2-phenylcyclopropan-1-amine;
CAS Number	155-09-9 ;
PubChem CID	19493;
DrugBank	DB00752 ;
ChemSpider	18369 ;
UNII	3E3V44J4Z9;
KEGG	D08625 ;
ChEBI	CHEBI:9652 ;
ChEMBL	ChEMBL1179 ;
ECHA InfoCard	100.005.312
Chemical and physical data
Formula	C9H11N
Molar mass	133.194 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES c1cccc(c1)[C@@H]2C[C@H]2N;
	InChI InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1 ; Key:AELCINSCMGFISI-DTWKUNHWSA-N ;
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Tranylcypromine, sold under the brand name Parnate among others,^[1] is a monoamine oxidase inhibitor (MAOI).^[4]^[7] More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO).^[4]^[7] It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively. It is also effective in the treatment of ADHD.^[8]^[9]

Tranylcypromine is a cyclopropylamine formed pro forma from the cyclization of amphetamine's side chain; therefore, it is classified as a substituted amphetamine.

^ ^a ^b "International brands for Tranylcypromine". Drugs.com. Retrieved 17 April 2016.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e Williams DA (2007). "Antidepressants". In Foye WO, Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Hagerstwon, USA: Lippincott Williams & Wilkins. pp. 590–1. ISBN 978-0-7817-6879-5.
^ "Tranylcypromine". www.drugbank.ca. Retrieved 2019-12-06.
^ Baker GB, Urichuk LJ, McKenna KF, Kennedy SH (June 1999). "Metabolism of monoamine oxidase inhibitors". Cellular and Molecular Neurobiology. 19 (3): 411–26. doi:10.1023/a:1006901900106. PMID 10319194. S2CID 21380176.
^ ^a ^b Baldessarini RJ (2005). "17. Drug therapy of depression and anxiety disorders". In Brunton LL, Lazo JS, Parker KL (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics. New York: McGraw-Hill. ISBN 978-0-07-142280-2.
^ Zametkin A, Rapoport JL, Murphy DL, Linnoila M, Ismond D. Treatment of hyperactive children with monoamine oxidase inhibitors. I. Clinical efficacy. Arch Gen Psychiatry. 1985 Oct;42(10):962-6. doi: 10.1001/archpsyc.1985.01790330042005. PMID: 3899047.
^ Levin GM. Attention-deficit hyperactivity disorder: the pharmacist's role. Am Pharm. 1995 Nov;NS35(11):10-20. PMID: 8533716.

[generics-1] "International brands for Tranylcypromine". Drugs.com. Retrieved 17 April 2016.

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[3] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[Foye's-4] Williams DA (2007). "Antidepressants". In Foye WO, Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Hagerstwon, USA: Lippincott Williams & Wilkins. pp. 590–1. ISBN 978-0-7817-6879-5.

[5] "Tranylcypromine". www.drugbank.ca. Retrieved 2019-12-06.

[6] Baker GB, Urichuk LJ, McKenna KF, Kennedy SH (June 1999). "Metabolism of monoamine oxidase inhibitors". Cellular and Molecular Neurobiology. 19 (3): 411–26. doi:10.1023/a:1006901900106. PMID 10319194. S2CID 21380176.

[G&G-7] Baldessarini RJ (2005). "17. Drug therapy of depression and anxiety disorders". In Brunton LL, Lazo JS, Parker KL (eds.). Goodman & Gilman's The Pharmacological Basis of Therapeutics. New York: McGraw-Hill. ISBN 978-0-07-142280-2.

[8] Zametkin A, Rapoport JL, Murphy DL, Linnoila M, Ismond D. Treatment of hyperactive children with monoamine oxidase inhibitors. I. Clinical efficacy. Arch Gen Psychiatry. 1985 Oct;42(10):962-6. doi: 10.1001/archpsyc.1985.01790330042005. PMID: 3899047.

[9] Levin GM. Attention-deficit hyperactivity disorder: the pharmacist's role. Am Pharm. 1995 Nov;NS35(11):10-20. PMID: 8533716.

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Clinical data
(1S,2R)-(−)-tranylcypromine (top), (1R,2S)-(+)-tranylcypromine (bottom)
Trade names	Parnate, many generics^[1]
Other names	trans-2-phenylcyclopropylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a682088
Pregnancy category	AU: B2
Routes of administration	Oral
ATC code	N06AF04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[3] CA: ℞-only UK: POM (Prescription only) US: WARNING^[2]Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	50%^[4]
Metabolism	Liver^[5]^[6]
Elimination half-life	2.5 hours^[4]
Excretion	Urine, Feces^[4]
Identifiers
IUPAC name (±)-trans-2-phenylcyclopropan-1-amine or rel-(1R,2S)-2-phenylcyclopropan-1-amine
CAS Number	155-09-9^Y
PubChem CID	19493
DrugBank	DB00752^Y
ChemSpider	18369^Y
UNII	3E3V44J4Z9
KEGG	D08625^N
ChEBI	CHEBI:9652^N
ChEMBL	ChEMBL1179^N
ECHA InfoCard	100.005.312
Chemical and physical data
Formula	C₉H₁₁N
Molar mass	133.194 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES c1cccc(c1)[C@@H]2C[C@H]2N
InChI InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1^Y Key:AELCINSCMGFISI-DTWKUNHWSA-N^Y
^NY (what is this?) (verify)