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P134

Sigma-Aldrich

(−)-Pentazocine

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C19H27NO
CAS Number:
359-83-1
Molecular Weight:
285.42
EC Number:
206-634-6
MDL number:
MFCD00869259
UNSPSC Code:
12352200
PubChem Substance ID:
329820088
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

drug control

USDEA Schedule IV; Home Office Schedule 3; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIC (Portugal)

storage condition

protect from light

color

white

solubility

DMSO: >10 mg/mL

originator

Sanofi Aventis

storage temp.

room temp

SMILES string

C[C@@H]1[C@@H]2Cc3ccc(O)cc3[C@@]1(C)CCN2C\C=C(\C)C

InChI

1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1

InChI key

VOKSWYLNZZRQPF-CCKFTAQKSA-N

Biochem/physiol Actions

Pentazocine is an analgesic with both agonist and antagonist activities. It acts as a κ- and σ-opioid receptor agonist and partial mu-receptor antagonist. Pentazocine pre-treatment reduces the frequency of fentanyl-induced cough and improves the anesthetic effect.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ralph Holl et al.
Journal of medicinal chemistry, 52(7), 2126-2137 (2009-02-27)
A series of 6,8-diazabicyclo[3.2.2]nonane derivatives bearing two aromatic moieties was prepared, the affinity toward sigma(1) and sigma(2) receptors was investigated, and the growth inhibition of six human tumor cell lines was determined. The enantiopure bicyclic ketones 5a ((+)-(1S,5S)-6-allyl-8-(4-methoxybenzyl)-6,8-diazabicyclo[3.2.2]nonane-2,7,9-trione) and 5b
Ling-Wei Hsin et al.
Journal of medicinal chemistry, 53(3), 1392-1396 (2010-01-09)
A series of enantiomeric N-substituted 2,3,4,4a,5,6,7,7a-octahydro-1H-benzofuro[3,2-e]isoquinolines was synthesized. The (-)-enantiomers had much greater kappa-, mu-, and delta-opioid receptor binding affinity than the corresponding (+)-enantiomers. Compounds (-)-1a, (-)-1b, and (-)-1c displayed subnanomolar binding affinity for the mu-receptor, and (-)-1b had a
Christian Geiger et al.
Journal of medicinal chemistry, 50(24), 6144-6153 (2007-10-31)
All possible stereoisomeric alcohols (6-benzyl-8-(4-methoxybenzyl)-6,8-diazabicyclo[3.2.2]nonan-2-ol) and methyl ethers (6-benzyl-2-methoxy-8-(4-methoxybenzyl)-6,8-diazabicyclo[3.2.2]nonane) are prepared from (R)- and (S)-glutamate. A Dieckmann analogous cyclization, which makes use of trapping the primary cyclization product with Me3SiCl, generates the bicyclic framework. Stereoselective LiBH4 reduction and Mitsunobu inversion
Carmen Abate et al.
Journal of medicinal chemistry, 54(4), 1022-1032 (2011-01-15)
1-Cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) represents an excellent lead candidate for therapeutic and/or diagnostic applications in oncology. However, because its utility is limited by its relatively high degree of lipophilicity, novel analogues of 1 with reduced lipophilic character were designed by substituting
Eva Grosse Maestrup et al.
Bioorganic & medicinal chemistry, 19(1), 393-405 (2010-12-04)
In order to develop a fluorinated radiotracer for imaging of σ(1) receptors in the central nervous system a series of (2-fluoroethyl) substituted spirocyclic piperidines 3 has been prepared. In the key step of the synthesis 2-bromocinnamaldehyde acetal 5 was added
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