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MedKoo Cat#: 326885 | Name: Delequamine HCl

Description:

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

Delequamine, also known RS-15385 or RS-15385-197 (HCl salt), is a potent and selective alpha 2-adrenoceptor antagonist. RS-15385-197 had a pKi of 9.45 for alpha 2-adrenoceptors in the rat cortex (pA2 in the guinea-pig ileum of 9.72). RS-15385-197 was highly selective for alpha 2-adrenoceptors over other receptors: the compound showed low affinity for 5-HT1A (pKi 6.50) and 5-HT1D (pKi 7.00) receptor subtypes, and even lower affinity (pKi < or = 5) for other 5-HT receptor subtypes, dopamine receptors, muscarinic cholinoceptors, beta-adrenoceptors and dihydropyridine binding sites.

Chemical Structure

Delequamine HCl
Delequamine HCl
CAS#119942-75-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 326885

Name: Delequamine HCl

CAS#: 119942-75-5 (HCl)

Chemical Formula: C18H27ClN2O3S

Exact Mass:

Molecular Weight: 386.94

Elemental Analysis: C, 55.87; H, 7.03; Cl, 9.16; N, 7.24; O, 12.40; S, 8.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
119942-75-5 (HCl) 119905-05-4 (free base)
Synonym
RS-15385; RS 15385; RS15385; RS-15385-197; Delequamine; Delequamine HCl.
IUPAC/Chemical Name
(8aR,12aS,13aS)-5,8,8a,9,10,11,12,12a,13,13a-Decahydro-3-methoxy-12-(methylsulfonyl)-6H-isoquino(2,1-g)(1,6)naphthyridine monohydrochloride
InChi Key
ITJOISLXCMAIOC-CVLULELNSA-N
InChi Code
InChI=1S/C18H26N2O3S.ClH/c1-23-15-5-6-16-13(10-15)7-9-19-12-14-4-3-8-20(24(2,21)22)17(14)11-18(16)19;/h5-6,10,14,17-18H,3-4,7-9,11-12H2,1-2H3;1H/t14-,17+,18+;/m1./s1
SMILES Code
O=S(N1CCC[C@]2([H])CN(CCC3=C4C=CC(OC)=C3)[C@@]4([H])C[C@]12[H])(C)=O.[H]Cl
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 386.94 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: Padma-Nathan H, Christ G, Adaikan G, Becher E, Brock G, Carrier S, Carson C, Corbin J, Francis S, DeBusk R, Eardley I, Hedlund H, Hutter A, Jackson G, Kloner R, Lin CS, McVary K, McCullough A, Nehra A, Porst H, Schulman C, Seftel A, Sharlip I, Stief C, Teloken C. Pharmacotherapy for erectile dysfunction. J Sex Med. 2004 Sep;1(2):128-40. Erratum in: J Sex Med. 2005 Jan;2(1):158. Lin, Shin [corrected to Lin, Ching-Shwun]. PubMed PMID: 16422967. 2: Kim NN, Min K, Huang YH, Goldstein I, Traish AM. Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina. Life Sci. 2002 Nov 1;71(24):2909-20. PubMed PMID: 12377271. 3: Allard J, Giuliano F. Central nervous system agents in the treatment of erectile dysfunction: how do they work? Curr Urol Rep. 2001 Dec;2(6):488-94. Review. PubMed PMID: 12084236. 4: Hume SP, Hirani E, Opacka-Juffry J, Osman S, Myers R, Gunn RN, McCarron JA, Clark RD, Melichar J, Nutt DJ, Pike VW. Evaluation of [O-methyl-11C]RS-15385-197 as a positron emission tomography radioligand for central alpha2-adrenoceptors. Eur J Nucl Med. 2000 May;27(5):475-84. PubMed PMID: 10853800. 5: Bancroft J. Effects of alpha-2 blockade on sexual response: experimental studies with delequamine (RS15385). Int J Impot Res. 2000 Mar;12 Suppl 1:S64-69. Review. PubMed PMID: 10845766. 6: Saenz de Tejada I, Kim NN, Goldstein I, Traish AM. Regulation of pre-synaptic alpha adrenergic activity in the corpus cavernosum. Int J Impot Res. 2000 Mar;12 Suppl 1:S20-25. Review. PubMed PMID: 10845761. 7: Bancroft J. Effects of alpha-2 blockade on sexual response: experimental studies with Delequamine (RS15385). Int J Impot Res. 2000 Mar;12(S1):S64-S69. PubMed PMID: 10849567. 8: Spedding M, Newman-Tancredi A, Millan MJ, Dacquet C, Michel AN, Jacoby E, Vickery B, Tallentire D. Interaction of the anxiogenic agent, RS-30199, with 5-HT1A receptors: modulation of sexual activity in the male rat. Neuropharmacology. 1998 Jun;37(6):769-80. PubMed PMID: 9707291. 9: Gonzalez MI, Patmore L, Wilson CA. Effect of delequamine (RS15385) on female sexual behaviour in the rat. Eur J Pharmacol. 1996 Sep 19;312(1):1-6. PubMed PMID: 8891572. 10: Tallentire D, McRae G, Spedding M, Clark R, Vickery B. Modulation of sexual behaviour in the rat by a potent and selective alpha 2-adrenoceptor antagonist, delequamine (RS-15385-197). Br J Pharmacol. 1996 May;118(1):63-72. PubMed PMID: 8733577; PubMed Central PMCID: PMC1909492. 11: Redfern WS, Williams A. A re-evaluation of the role of alpha 2-adrenoceptors in the anxiogenic effects of yohimbine, using the selective antagonist delequamine in the rat. Br J Pharmacol. 1995 Oct;116(3):2081-9. PubMed PMID: 8640349; PubMed Central PMCID: PMC1908953. 12: Bancroft J, Munoz M, Beard M, Shapiro C. The effects of a new alpha-2 adrenoceptor antagonist on sleep and nocturnal penile tumescence in normal male volunteers and men with erectile dysfunction. Psychosom Med. 1995 Jul-Aug;57(4):345-56. PubMed PMID: 7480564. 13: Redfern WS, MacLean MR, Clague RU, McGrath JC. The role of alpha 2-adrenoceptors in the vasculature of the rat tail. Br J Pharmacol. 1995 Apr;114(8):1724-30. PubMed PMID: 7599941; PubMed Central PMCID: PMC1510371. 14: Munoz M, Bancroft J, Beard M. Evaluating the effects of an alpha-2 adrenoceptor antagonist on erectile function in the human male. 2. The erectile response to erotic stimuli in men with erectile dysfunction, in relation to age and in comparison with normal volunteers. Psychopharmacology (Berl). 1994 Aug;115(4):471-7. PubMed PMID: 7871091. 15: Munoz M, Bancroft J, Turner M. Evaluating the effects of an alpha-2 adrenoceptor antagonist on erectile function in the human male. 1. The erectile response to erotic stimuli in volunteers. Psychopharmacology (Berl). 1994 Aug;115(4):463-70. PubMed PMID: 7871090. 16: MacKinnon AC, Spedding M, Brown CM. Sodium modulation of 3H-agonist and 3H-antagonist binding to alpha 2-adrenoceptor subtypes. Br J Pharmacol. 1993 Jun;109(2):371-8. PubMed PMID: 8102928; PubMed Central PMCID: PMC2175701. 17: MacKinnon AC, Stewart M, Olverman HJ, Spedding M, Brown CM. [3H]p-aminoclonidine and [3H]idazoxan label different populations of imidazoline sites on rat kidney. Eur J Pharmacol. 1993 Feb 23;232(1):79-87. PubMed PMID: 8096190. 18: Redfern WS, MacKinnon AC, Brown CM, Martin AB, Kilpatrick AT, Clague RU, Spedding M. Modulation of central noradrenergic function by RS-15385-197. Br J Pharmacol. 1993 Feb;108(2):526-33. PubMed PMID: 8095421; PubMed Central PMCID: PMC1907981. 19: Brown CM, MacKinnon AC, Redfern WS, Hicks PE, Kilpatrick AT, Small C, Ramcharan M, Clague RU, Clark RD, MacFarlane CB, et al. The pharmacology of RS-15385-197, a potent and selective alpha 2-adrenoceptor antagonist. Br J Pharmacol. 1993 Feb;108(2):516-25. PubMed PMID: 8095420; PubMed Central PMCID: PMC1908001. 20: MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM. [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. PubMed PMID: 1327384; PubMed Central PMCID: PMC1907641.