Iproniazid

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Iproniazid
Iproniazid.svg
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy
category
  •  ?
Routes of
administration
?
ATC code N06AF05 (WHO)
Legal status
Legal status
  •  ?
Pharmacokinetic data
Bioavailability ?
Metabolism ?
Biological half-life ?
Excretion ?
Identifiers
CAS Number 54-92-2 YesY
PubChem (CID) 3748
DrugBank DB04818 YesY
ChemSpider 3617 YesY
UNII D892HFI3XA YesY
KEGG D02579 YesY
ChEMBL CHEMBL92401 YesY
ECHA InfoCard 100.000.199
Chemical and physical data
Formula C9H13N3O
Molar mass 179.219 g/mol
3D model (Jmol) Interactive image
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Iproniazid (Marsilid, Rivivol, Euphozid, Iprazid, Ipronid, Ipronin) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class.[1][2] It was discontinued in most of the world in the 1960s, but remained in use in France until fairly recently.[3]

Iproniazid was originally developed for the treatment of tuberculosis,[1] but in 1952, its antidepressant properties were discovered when researchers noted that patients given isoniazid became inappropriately happy.[1] Subsequently N-isopropyl addition led to development as an antidepressant and was approved for use in 1958.[1] It was withdrawn a few years later in 1961 due to a high incidence of hepatitis, and was replaced by less hepatotoxic drugs such as phenelzine and isocarboxazid.[1]

Although iproniazid was one of the first antidepressants ever marketed, amphetamine (marketed as Benzedrine from 1935, for "mild depression", amid other indications)[4] predates it; and frankincense has been marketed traditionally for millennia for, among other things, altering mood, although it was not until 2012 that one of the components of its smoke was found to have antidepressant effects in mice.[5] [6] [7]

See also[edit]

References[edit]

  1. ^ a b c d e Robert A. Maxwell; Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. pp. 143–154. ISBN 0-89603-180-2. ISBN 9780896031807. 
  2. ^ Fagervall I, Ross SB (April 1986). "Inhibition of monoamine oxidase in monoaminergic neurones in the rat brain by irreversible inhibitors". Biochemical pharmacology. 35 (8): 1381–7. doi:10.1016/0006-2952(86)90285-6. PMID 2870717. 
  3. ^ Maille F, Duvoux C, Cherqui D, Radier C, Zafrani ES, Dhumeaux D (October 1999). "[Auxiliary hepatic transplantation in iproniazid-induced subfulminant hepatitis. Should iproniazid still be sold in France?]". Gastroenterol. Clin. Biol. (in French). 23 (10): 1083–5. PMID 10592880. 
  4. ^ Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present – a pharmacological and clinical perspective". J. Psychopharmacol. 27 (6): 479–96. doi:10.1177/0269881113482532. PMC 3666194Freely accessible. PMID 23539642. 
  5. ^ Moussaieff, Arieh; Rimmerman, Neta; Bregman, Tatiana; Straiker, Alex; Felder, Christian C.; Shoham, Shai; Kashman, Yoel; Huang, Susan M.; Lee, Hyosang; Shohami, Esther; Mackie, Ken; Caterina, Michael J.; Walker, J. Michael; Fride, Ester; Mechoulam, Raphael (August 2008). "Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brain". 22 (8). The FASEB Journal: 3024–3034. doi:10.1096/fj.07-101865. PMC 2493463Freely accessible. PMID 18492727. 
  6. ^ Moussaieff, A; Gross, M; Nesher, E; Tikhonov, T; Yadid, G; Pinhasov, A (2012). "Incensole acetate reduces depressive-like behavior and modulates hippocampal BDNF and CRF expression of submissive animals". J Psychopharmacol. 26 (12). doi:10.1177/0269881112458729. PMID 23015543. 
  7. ^ Drahl, Carmen (22 December 2008). "Frankincense And Myrrh". Chemical & Engineering News. 86 (51): 38. doi:10.1021/cen-v086n051.p038. ISSN 0009-2347.