PIPEROXAN

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H19NO2
Molecular Weight	233.3062
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(C1COC2=CC=CC=C2O1)N3CCCCC3

InChI

InChIKey=LYKMMUBOEFYJQG-UHFFFAOYSA-N

InChI=1S/C14H19NO2/c1-4-8-15(9-5-1)10-12-11-16-13-6-2-3-7-14(13)17-12/h2-3,6-7,12H,1,4-5,8-11H2

HIDE SMILES / InChI

Molecular Formula	C14H19NO2
Molecular Weight	233.3062
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugfuture.com/chemdata/piperoxan.html | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 989, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ | Lemke, T.L., Williams, D.A. (2008) Foye's Principles of Medicinal Chemistry, page 1010, retrieved from: https://books.google.ru/books?id=R0W1ErpsQpkC | Usdin, E. et al. (2016) Endorphins in Mental Health Research, page 285, retrieved from: https://books.google.ru/books?id=lNhlCwAAQBAJ | Fuxe, K. et al. (2013) Central Adrenaline Neurons, page 136, retrieved from: https://books.google.ru/books?id=pIOfAgAAQBAJ

Piperoxan is the first antihistamine was discovered. Piperoxan protected guinea pigs against histamine-induced bronchospasm. The piperoxan has been used to provoke anxiety behaviors in the monkey. Piperoxan is an alpha-adrenergic antagonist. Piperoxan has been claimed to preferentially block presynaptic alpha-adrenoreceptors leading to an increase in noradrenaline release and by this way the postsynaptic alpha-adrenoreceptors blockade may be overcome. There was clear evidence that piperoxan enhanced myocardial performance. Piperoxan is a diagnostic aid used in studies of hypertension.

Approval Year

Doses

Dose	Population	Adverse events
10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13252923/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/13252923/	Sources: https://pubmed.ncbi.nlm.nih.gov/13252923/
15 mg single, intravenous Recommended Dose: 15 mg Route: intravenous Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14850300/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/14850300/	Other AEs: Pulse rapid... Other AEs: Pulse rapid (16 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/14850300/

AEs

AE	Significance	Dose	Population
Pulse rapid	16 patients	15 mg single, intravenous Recommended Dose: 15 mg Route: intravenous Route: single Dose: 15 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14850300/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/14850300/

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0039CZ	https://www.aablocks.com/goods/Goods/detail?id=AA0039CZ
Aaron Chemicals	AR003A4R	http://www.aaronchem.com/59-39-2
abcr GmbH	AB494371	http://www.abcr.com/shop/en/AB494371
Alichem	129009281	http://www.alichem.com/en/products/59-39-2.html
Angene	AGN-PC-0JK7G5	http://www.angenechemical.com/productshow/AGN-PC-0JK7G5.html
BioChemPartner	BCP19333	http://www.biochempartner.com/59-39-2-BCP19333
BLD Pharm	BD148262	http://www.bldpharm.com/products/59-39-2.html
ChemMol	49425911	http://www.chemmol.com/chemmol/49425911.html
Chemspace	CSSB00030741262	https://chem-space.com/CSSB00030741262
eNovation Chemicals	D556398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D556398
eNovation Chemicals	D584215	https://www.enovationchem.com/ProductDetails.asp?ProductID=D584215
OChem	11943	http://www.ocheminc.com/index.php?act=psearch&pid=059P392
Smolecule	S603919	https://www.smolecule.com/products/s603919
THE BioTek	bt-367420	https://www.thebiotek.com/product/others/bt-367420

PubMed

Title	Date	PubMed
Role of alpha-2 adrenergic receptors in anti-ulcer effect mechanism of estrogen and luteinising hormone on rats.	2009-04	19340627
Nasal trigeminal inputs release the A5 inhibition received by the respiratory rhythm generator of the mouse neonate.	2004-02	14561692
Development of a segmented model for a continuous electrophoretic moving bed enantiomer separation.	2003-12-06	14656145
Continuous fractionation of enantiomer pairs in free solution using an electrophoretic analog of simulated moving bed chromatography.	2002-04-12	12058940
Use of dyes to investigate migration of the chiral selector in CFFE and the impact on the chiral separations.	2001-08-15	11534728
Antagonists of adenosine and alpha-2-adrenoceptors reverse the anticonvulsant effects of tizanidine in DBA/2 mice.	1989-03	2566944
Norepinephrine inhibition of pulsatile LH release: receptor specificity.	1986-02	3953791
Pharmacological properties of (N-dicyclopropylmethyl) amino-2-oxazoline (S 3341), an alpha-2 adrenoceptor agonist.	1985-07-01	2866274
[Comparative study of piperoxan and 2-(2-imidazolinyl)-1, 4-benzodioxane (170 150) on pre- and postsynaptic receptors in the rat].	1982-07-01	6290793
Pharmacological characteristics of spinal alpha-adrenoreceptors in rats.	1981-03	6121810
The role of alpha receptors in the facilitation of the chemoreflex and inhibition of the carotid occlusion reflex by clonidine.	1980	6256140
A comparison of the cardiovascular effects of centrally administered clonidine and adrenaline in the anaesthetized rat.	1979-01	32359
Cardiovascular changes in anaesthetised rats after the intra-hypothalamic administration of adrenaline.	1978	755652
Differentiation of drugs acting centrally upon the cardiovascular system by means of sympathetic and vagal responses.	1978	39714

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:34 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:34 GMT 2025`
Record UNII	9ZCS27634Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

933F

Preferred Name

English

PIPEROXAN

Official Name

English

FOURNEAU-933

Common Name

English

(±)-PIPEROXANE

Common Name

English

F-933

Code

English

piperoxan [INN]

Common Name

English

PIPEROXAN [MI]

Common Name

English

PIPEROXANE

Common Name

English

(RS)-PIPEROXANE

Common Name

English

PIPERIDINE, 1-(1,4-BENZODIOXAN-2-YLMETHYL)-

Systematic Name

English

BENODAINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713