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MedKoo Cat#: 598214 | Name: Pentazocine lactate

Description:

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

Pentazocine lactate is the first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. Pentazocine lactate is discontinued.

Chemical Structure

Pentazocine lactate
Pentazocine lactate
CAS#17146-95-1

Theoretical Analysis

MedKoo Cat#: 598214

Name: Pentazocine lactate

CAS#: 17146-95-1

Chemical Formula: C22H33NO4

Exact Mass:

Molecular Weight: 375.50

Elemental Analysis: C, 70.37; H, 8.86; N, 3.73; O, 17.04

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Pentazocine lactate; Liticon; Pentalgine; Talwin; Talwin Injection;
IUPAC/Chemical Name
(2S,6S,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 2-hydroxypropanoate
InChi Key
QNLDTXPVZPRSAM-PHMSSXDFSA-N
InChi Code
InChI=1S/C19H27NO.C3H6O3/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19;1-2(4)3(5)6/h5-7,12,14,18,21H,8-11H2,1-4H3;2,4H,1H3,(H,5,6)/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.CC(O)C(O)=O
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 375.50 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: Mori T, Ohya J, Itoh T, Ise Y, Shibasaki M, Suzuki T. Effects of (+)-pentazocine on the antinociceptive effects of (-)-pentazocine in mice. Synapse. 2015 Mar;69(3):166-71. doi: 10.1002/syn.21799. Epub 2015 Jan 13. PubMed PMID: 25559075. 2: Mori T, Itoh T, Yoshizawa K, Ise Y, Mizuo K, Saeki T, Komiya S, Masukawa D, Shibasaki M, Suzuki T. Involvement of μ- and δ-opioid receptor function in the rewarding effect of (±)-pentazocine. Addict Biol. 2015 Jul;20(4):724-32. doi: 10.1111/adb.12169. Epub 2014 Jul 27. PubMed PMID: 25065832. 3: Shu H, Wang Z, Ye F, Li Q, Dou Y, Lin Y, Huang W, Xiao X. High-dose pentazocine antagonizes the antinociception induced by high-dose morphine. Life Sci. 2015 Jun 1;130:1-6. doi: 10.1016/j.lfs.2015.02.023. Epub 2015 Mar 25. PubMed PMID: 25817230. 4: Kumar D, Gupta A, Sharma VP, Yadav G, Singh A, Verma AK. Pentazocine-induced contractures: Dilemma in management. Indian J Pharmacol. 2015 Jul-Aug;47(4):451-3. doi: 10.4103/0253-7613.161276. PubMed PMID: 26288482; PubMed Central PMCID: PMC4527072. 5: Kurogi K, Chen M, Lee Y, Shi B, Yan T, Liu MY, Sakakibara Y, Suiko M, Liu MC. Sulfation of buprenorphine, pentazocine, and naloxone by human cytosolic sulfotransferases. Drug Metab Lett. 2012 Jun 1;6(2):109-15. PubMed PMID: 22946908. 6: Olateju SO, Adenekan AT, Olufolabi AJ, Owojuyigbe AM, Adetoye AO, Ajenifuja KO, Olowookere SA, Faponle AF. PENTAZOCINE VERSUS PENTAZOCINE WITH RECTAL DICLOFENAC FOR POSTOPERATIVE PAIN RELIEF AFTER CESAREAN SECTION- A DOUBLE BLIND RANDOMIZED PLACEBO CONTROLLED TRIAL IN A LOW RESOURCE AREA. Middle East J Anaesthesiol. 2016 Feb;23(4):443-8. PubMed PMID: 27382814. 7: Kimura S, Ohi Y, Haji A. Mechanisms of pentazocine-induced ventilatory depression and antinociception in anesthetized rats. J Pharmacol Sci. 2016 Mar;130(3):181-4. doi: 10.1016/j.jphs.2016.03.003. Epub 2016 Mar 11. PubMed PMID: 27021234. 8: Hirabayashi M, Imamachi N, Sakakihara M, Saito Y. [Treatment of intrathecal fentanyl-induced itch with pentazocine: a case report]. Masui. 2014 Jun;63(6):696-9. Japanese. PubMed PMID: 24979869. 9: Miller RR. Clinical effects of pentazocine in hospitalized medical patients. J Clin Pharmacol. 1975 Feb-Mar;15(2-3):198-205. PubMed PMID: 1123460. 10: Oyake H, Onuki K, Yamanishi Y, Asami T, Onuki N, Yoshikawa S, Shimada J, Nagasaka H. [Effect of pentazocine on the bispectral index during nitrous oxide-sevoflurane anesthesia]. Masui. 2011 Oct;60(10):1128-34. Japanese. PubMed PMID: 22111350. 11: Chen Q, Huo X, Yang Z, She X. Asymmetric syntheses of (-)-pentazocine and (-)-eptazocine through an aza-Prins cyclization. Chem Asian J. 2012 Nov;7(11):2543-6. doi: 10.1002/asia.201200505. Epub 2012 Aug 21. PubMed PMID: 22907930. 12: Zafar S, Najam Y, Arif Z, Hafeez A. A randomized controlled trial comparing Pentazocine and Chamomilla recutita for labor pain relief. Homeopathy. 2016 Feb;105(1):66-70. doi: 10.1016/j.homp.2015.09.003. Epub 2015 Oct 31. PubMed PMID: 26827999. 13: Shu H, Hayashida M, Arita H, Huang W, Zhang H, An K, Wu G, Hanaoka K. Pentazocine-induced antinociception is mediated mainly by μ-opioid receptors and compromised by κ-opioid receptors in mice. J Pharmacol Exp Ther. 2011 Aug;338(2):579-87. doi: 10.1124/jpet.111.179879. Epub 2011 May 4. PubMed PMID: 21543510. 14: Ide S, Minami M, Uhl GR, Satoh M, Sora I, Ikeda K. (-)-Pentazocine induces visceral chemical antinociception, but not thermal, mechanical, or somatic chemical antinociception, in μ-opioid receptor knockout mice. Mol Pain. 2011 Apr 10;7:23. doi: 10.1186/1744-8069-7-23. PubMed PMID: 21477373; PubMed Central PMCID: PMC3090351. 15: Chawla R, Arora MK, Saksena R, Gode GR. Efficacy & dose-response of intrathecal pentazocine for post-operative pain relief. Indian J Med Res. 1989 Jun;90:220-3. PubMed PMID: 2767747. 16: Ohsawa M, Hayashi SS, Kamei J. Effect of acute topical application of +-pentazocine on the mechanical allodynia in diabetic mice. Eur J Pharmacol. 2010 Sep 1;641(1):49-53. doi: 10.1016/j.ejphar.2010.05.005. Epub 2010 May 21. PubMed PMID: 20546721. 17: Goldstein G. Pentazocine. Drug Alcohol Depend. 1985 Feb;14(3-4):313-23. Review. PubMed PMID: 3888578. 18: Xu HQ, Xing JM, Jia R. [Clinical observation of pentazocine for postoperative intravenous analgesia in patients with lumbar herniation]. Zhongguo Gu Shang. 2010 Nov;23(11):838-40. Chinese. PubMed PMID: 21254677. 19: Gilbert MS, Forman RS, Moylan DS, Caruso FS. Butorphanol: a double-blind comparison with pentazocine in post-operative patients with moderate to severe pain. J Int Med Res. 1976;4(4):255-64. PubMed PMID: 799996. 20: Steiner R. Rx--Talwin (Pentazocaine lactate). J Hosp Dent Pract. 1968 Apr;11(2):40-2. PubMed PMID: 5242527.

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