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=C(O1)C=CC=C2)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 n = 1 Health Status: unhealthy Condition: overdose of adrenaline (5 mg) Age Group: adult Sex: unknown Population Size: 1 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 n = 62 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Population Size: 62 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 n = 62 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: unknown Population Size: 62 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
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
BLD Pharm	BD148262	http://www.bldpharm.com/products/59-39-2.html
BioChemPartner	BCP19333	http://www.biochempartner.com/59-39-2-BCP19333
ChemMol	49425911	http://www.chemmol.com/chemmol/49425911.html
Chemspace	CSSB00030741262	https://chem-space.com/CSSB00030741262
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
abcr GmbH	AB494371	http://www.abcr.com/shop/en/AB494371
eNovation Chemicals	D556398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D556398
eNovation Chemicals	D584215	https://www.enovationchem.com/ProductDetails.asp?ProductID=D584215

PubMed

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

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:26:00 UTC 2023` Edited by `admin` on `Fri Dec 15 15:26:00 UTC 2023`
Record UNII	9ZCS27634Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

933F

Code

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