Synonym
Clocinnamox; NIH10989; NIH-10989; NIH 10989
IUPAC/Chemical Name
2-Propenamide, 3-(4-chlorophenyl)-N-((5alpha)-17-(cyclopropylmethyl)-4,5-epoxy-3-hydroxy-6-oxomorphinan-14-yl)-, monomethanesulfonate
InChi Key
XAXNKAGAUFXFDO-JVJDXIHNSA-N
InChi Code
InChI=1S/C29H29ClN2O4.CH4O3S/c30-20-7-3-17(4-8-20)5-10-24(35)31-29-12-11-22(34)27-28(29)13-14-32(16-18-1-2-18)23(29)15-19-6-9-21(33)26(36-27)25(19)28;1-5(2,3)4/h3-10,18,23,27,33H,1-2,11-16H2,(H,31,35);1H3,(H,2,3,4)/b10-5+;/t23-,27+,28+,29-;/m1./s1
SMILES Code
O=C(N[C@]1([C@]2([C@@]3([H])O4)C5=C4C(O)=CC=C5C[C@H]1N(CC6CC6)CC2)CCC3=O)/C=C/C7=CC=C(Cl)C=C7.CS(=O)(O)=O
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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
601.11
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.
| 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: Paronis CA, Woods JH. Clocinnamox dose-dependently antagonizes morphine- analgesia and [3H]DAMGO binding in rats. Eur J Pharmacol. 1997 Oct 15;337(1):27-34. doi: 10.1016/s0014-2999(97)01296-x. PMID: 9389377.
2: Butelman ER, Negus SS, Lewis JW, Woods JH. Clocinnamox antagonism of opioid suppression of schedule-controlled responding in rhesus monkeys. Psychopharmacology (Berl). 1996 Feb;123(4):320-4. doi: 10.1007/BF02246641. PMID: 8867870.
3: Walker EA, Young AM. Clocinnamox distinguishes opioid agonists according to relative efficacy in normal and morphine-treated rats trained to discriminate morphine. J Pharmacol Exp Ther. 2002 Jul;302(1):101-10. doi: 10.1124/jpet.302.1.101. PMID: 12065706.
4: Chan K, Brodsky M, Davis T, Franklin S, Inturrisi CE, Yoburn BC. The effect of the irreversible mu-opioid receptor antagonist clocinnamox on morphine potency, receptor binding and receptor mRNA. Eur J Pharmacol. 1995 Dec 12;287(2):135-43. doi: 10.1016/0014-2999(95)00488-2. PMID: 8749027.
5: Zernig G, Butelman ER, Lewis JW, Walker EA, Woods JH. In vivo determination of mu opioid receptor turnover in rhesus monkeys after irreversible blockade with clocinnamox. J Pharmacol Exp Ther. 1994 Apr;269(1):57-65. PMID: 8169852.
6: Zernig G, Lewis JW, Woods JH. Clocinnamox inhibits the intravenous self- administration of opioid agonists in rhesus monkeys: comparison with effects on opioid agonist-mediated antinociception. Psychopharmacology (Berl). 1997 Feb;129(3):233-42. doi: 10.1007/s002130050185. PMID: 9084061.
7: Burke TF, Woods JH, Lewis JW, Medzihradsky F. Irreversible opioid antagonist effects of clocinnamox on opioid analgesia and mu receptor binding in mice. J Pharmacol Exp Ther. 1994 Nov;271(2):715-21. PMID: 7965787.
8: Chan KW, Duttory A, Yoburn BC. Magnitude of tolerance to fentanyl is independent of mu-opioid receptor density. Eur J Pharmacol. 1997 Jan 29;319(2-3):225-8. doi: 10.1016/s0014-2999(96)00960-0. PMID: 9042594.
9: Comer SD, Burke TF, Lewis JW, Woods JH. Clocinnamox: a novel, systemically- active, irreversible opioid antagonist. J Pharmacol Exp Ther. 1992 Sep;262(3):1051-6. PMID: 1326622.
10: Zernig G, Burke T, Lewis JW, Woods JH. Mechanism of clocinnamox blockade of opioid receptors: evidence from in vitro and ex vivo binding and behavioral assays. J Pharmacol Exp Ther. 1996 Oct;279(1):23-31. PMID: 8858971.
