Iproniazide

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Iproniazide
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	?
Elimination half-life	?
Excretion	?
Identifiers
	IUPAC name N'-isopropylisonicotinohydrazide;
CAS Number	54-92-2 ;
PubChem CID	3748;
DrugBank	DB04818 ;
ChemSpider	3617 ;
UNII	D892HFI3XA;
KEGG	D02579 ;
ChEMBL	ChEMBL92401 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C9H13N3O
Molar mass	179.219 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(NNC(C)C)c1ccncc1;
	InChI InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13) ; Key:NYMGNSNKLVNMIA-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 up 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Subsequently N-isopropyl addition lead to development as an antidepressant and was approved for use in 1958.^[1] It was withdrawn a few years later in 1961 due to a high incidence of hepatitis, and was replaced by less hepatotoxic drugs such as phenelzine and isocarboxazid.^[1]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]

Synthesis

Condensation of isoniazid with acetone at the basic nitrogen gives the corresponding Schiff base. Catalytic hydrogenation affords the antidepressant iproniazid.

Prepd by treating isoniazid with isopropyl bromide in absolute alcohol in the presence of sodium.

Presumably, a third way would be to react the isonicotinic acid ester with acetone hydrazone,^[10] the same reactant used in the production of etazolate. Iproniazid would then be obtained after a reduction step.

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Robert A. Maxwell, Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. pp. 143–154. ISBN 0-89603-180-2. ISBN 9780896031807.
↑ 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.
↑ 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.
↑ 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 3666194. PMID 23539642.
↑ 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 2493463. PMID 18492727.
↑ 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.
↑ Drahl, Carmen (22 December 2008). "Frankincense And Myrrh". Chemical & Engineering News. 86 (51): 38. doi:10.1021/cen-v086n051.p038. ISSN 0009-2347.
↑ Template:Cite DOI
↑ McMillan et al., J. Am. Pharm. Assoc. Sci. Ed. 42, 457 (1953).
↑ "Simple Accordion with CSS & jQuery by Soh Tanaka". Orgsyn.org. Retrieved 2015-04-12.

Template:Antidepressants Template:Monoaminergics Template:Hydrazines

Template:Nervous-system-drug-stub

[bookDrug_discovery-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Robert A. Maxwell, Shohreh B. Eckhardt (1990). Drug discovery. Humana Press. pp. 143–154. ISBN 0-89603-180-2. ISBN 9780896031807.

[pmid2870717-2] 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.

[pmid10592880-3] 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.

[Amph_Uses_Dex-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 3666194. 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 2493463. 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.

[8] Template:Cite DOI

[9] McMillan et al., J. Am. Pharm. Assoc. Sci. Ed. 42, 457 (1953).

[10] "Simple Accordion with CSS & jQuery by Soh Tanaka". Orgsyn.org. Retrieved 2015-04-12.

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Iproniazide

Overview

Synthesis

See also

References

Navigation menu

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	?
Elimination half-life	?
Excretion	?
Identifiers
IUPAC name N'-isopropylisonicotinohydrazide
CAS Number	54-92-2^Y
PubChem CID	3748
DrugBank	DB04818^Y
ChemSpider	3617^Y
UNII	D892HFI3XA
KEGG	D02579^Y
ChEMBL	ChEMBL92401^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₉H₁₃N₃O
Molar mass	179.219 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(NNC(C)C)c1ccncc1
InChI InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)^Y Key:NYMGNSNKLVNMIA-UHFFFAOYSA-N^Y
(verify)