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MedKoo Cat#: 597703 | Name: Pentazocine, (-)-

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pentazocine, (-)- is a painkiller used to treat moderate to severe pain. It is believed to work by activating (agonizing) κ-opioid receptors (KOR) and blocking (antagonizing) μ-opioid receptors (MOR). Pentazocine, (-)- is discontinued.

Chemical Structure

Pentazocine, (-)-
Pentazocine, (-)-
CAS#7488-49-5

Theoretical Analysis

MedKoo Cat#: 597703

Name: Pentazocine, (-)-

CAS#: 7488-49-5

Chemical Formula: C19H27NO

Exact Mass: 285.2093

Molecular Weight: 285.43

Elemental Analysis: C, 79.95; H, 9.54; N, 4.91; O, 5.61

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Pentazocine, (-)-; L-Pentazocine; Levopentazocine; (-)-alpha-Pentazocine;
IUPAC/Chemical Name
(2R,6R,11R)-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-ol
InChi Key
VOKSWYLNZZRQPF-GDIGMMSISA-N
InChi Code
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+/m0/s1
SMILES Code
OC1=CC=C2C([C@]3(C)CCN(C/C=C(C)\C)[C@]([C@@H]3C)([H])C2)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 285.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Goldstein G. Pentazocine. Drug Alcohol Depend. 1985 Feb;14(3-4):313-23. Review. PubMed PMID: 3888578. 2: Swift JQ, Hargreaves KM. Pentazocine analgesia: is there a niche for Talwin Nx? Compendium. 1993 Aug;14(8):1048, 1050 passim; quiz 1060. Review. PubMed PMID: 8269439. 3: Legros J, Khalili-Varasteh H, Margetts G. Pharmacological study of pentazocine-naloxone combination: interest as a potentially non abusable oral form of pentazocine. Arch Int Pharmacodyn Ther. 1984 Sep;271(1):11-21. PubMed PMID: 6541897. 4: Yeh SY, Todd GD, Johnson RE, Gorodetzky CW, Lange WR. The pharmacokinetics of pentazocine and tripelennamine. Clin Pharmacol Ther. 1986 Jun;39(6):669-76. PubMed PMID: 3709032. 5: Challoner KR, McCarron MM, Newton EJ. Pentazocine (Talwin) intoxication: report of 57 cases. J Emerg Med. 1990 Jan-Feb;8(1):67-74. PubMed PMID: 2351801. 6: Baum C, Hsu JP, Nelson RC. The impact of the addition of naloxone on the use and abuse of pentazocine. Public Health Rep. 1987 Jul-Aug;102(4):426-9. PubMed PMID: 3112855; PubMed Central PMCID: PMC1477863. 7: Matsumoto RR, Bowen WD, Walker JM, Patrick SL, Zambon AC, Vo VN, Truong DD, De Costa BR, Rice KC. Dissociation of the motor effects of (+)-pentazocine from binding to sigma 1 sites. Eur J Pharmacol. 1996 Apr 22;301(1-3):31-40. PubMed PMID: 8773444. 8: Vaupel DB. Interactions between pentazocine and tripelennamine on autonomic and nociceptive measures in the dog. Pharmacol Biochem Behav. 1989 May;33(1):245-51. PubMed PMID: 2780781. 9: Saarialho-Kere U, Mattila MJ, Seppälä T. Pentazocine and codeine: effects on human performance and mood and interactions with diazepam. Med Biol. 1986;64(5):293-9. PubMed PMID: 3807445. 10: Kane FJ Jr, Pokorny A. Mental and emotional disturbance with pentazocine (Talwin) use. South Med J. 1975 Jul;68(7):808-11. PubMed PMID: 1154070. 11: North WC, Tielens DR. Comparison of butorphanol and pentazocine as postoperative analgesics. South Med J. 1979 May;72(5):578-80. PubMed PMID: 375401. 12: Kudo T, Kudo M, Kimura F, Ishihara H, Matsuki A. [Pharmacokinetics of ketamine and pentazocine during total intravenous anesthesia with droperidol, pentazocine and ketamine]. Masui. 1992 Nov;41(11):1772-6. Japanese. PubMed PMID: 1460754. 13: Takahashi H, Traystman RJ, Hashimoto K, London ED, Kirsch JR. Postischemic brain injury is affected stereospecifically by pentazocine in rats. Anesth Analg. 1997 Aug;85(2):353-7. PubMed PMID: 9249113. 14: Zabetian CP, Staley JK, Flynn DD, Mash DC. [3H]-(+)-pentazocine binding to sigma recognition sites in human cerebellum. Life Sci. 1994;55(20):PL389-95. PubMed PMID: 7968220. 15: Küçukhüseyin C. Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs. J Basic Clin Physiol Pharmacol. 2003;14(3):235-55. PubMed PMID: 14964736. 16: Cohen BM, Murphy B. The effects of pentazocine, a kappa agonist, in patients with mania. Int J Neuropsychopharmacol. 2008 Mar;11(2):243-7. Epub 2007 Sep 26. PubMed PMID: 17897484. 17: Pittman KA, Davison C. Quantitative determination of pentazocine in plasma and of pentazocine and metabolites in urine. J Pharm Sci. 1973 May;62(5):765-9. PubMed PMID: 4705681. 18: Kamei J, Iwamoto Y, Misawa M, Nagase H, Kasuya Y. Antitussive effect of (+/-) pentazocine in diabetic mice is mediated by delta-sites, but not by mu- or kappa-opioid receptors. Nihon Shinkei Seishin Yakurigaku Zasshi. 1994 Jun;14(3):147-52. PubMed PMID: 7941779. 19: Sugai N. [Recent developments in the pharmacology and clinical use of pentazocine]. Masui. 1991 Jul;40(7):1037-41. Review. Japanese. PubMed PMID: 1920775. 20: Graham JL, McCaughey W, Bell PF. Nalbuphine and pentazocine in an opioid-benzodiazepine sedative technique: a double-blind comparison. Ann R Coll Surg Engl. 1988 Jul;70(4):200-4. PubMed PMID: 3046465; PubMed Central PMCID: PMC2498783.

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