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MedKoo Cat#: 526508 | Name: Trimetoquinol HCl hydrate

Description:

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

Trimetoquinol is a nonselective, nonclassical β-adrenergic agonist. It's a potent and fast-acting bronchodilator in horses with heaves.

Chemical Structure

Trimetoquinol HCl hydrate
Trimetoquinol HCl hydrate
CAS#72534-66-8 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 526508

Name: Trimetoquinol HCl hydrate

CAS#: 72534-66-8 (HCl hydrate)

Chemical Formula: C19H26ClNO6

Exact Mass: 399.1449

Molecular Weight: 399.87

Elemental Analysis: C, 57.07; H, 6.55; Cl, 8.87; N, 3.50; O, 24.01

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 #
72534-66-8 (HCl hydrate) 18559-59-6 (HCl) 30418-38-3 (free base)
Synonym
RO 07-5965; RO07-5965 RO-07-5965; Trimetoquinol hydrochloride.
IUPAC/Chemical Name
(S)-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride hydrate
InChi Key
NYRVBYLXLHGXDP-UTLKBRERSA-N
InChi Code
InChI=1S/C19H23NO5.ClH.H2O/c1-23-17-7-11(8-18(24-2)19(17)25-3)6-14-13-10-16(22)15(21)9-12(13)4-5-20-14;;/h7-10,14,20-22H,4-6H2,1-3H3;1H;1H2/t14-;;/m0../s1
SMILES Code
OC1=CC2=C([C@H](CC3=CC(OC)=C(OC)C(OC)=C3)NCC2)C=C1O.[H]Cl.[H]O[H]
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, not in water
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 399.87 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: Camargo FC, Robinson NE, Dirikolu L, Berney C, Eberhart S, Derksen FJ, Lehner AF, May J, Hughes C, Tobin T. Plasma and urinary concentrations of trimetoquinol by LC-MS-MS following intravenous and intra-tracheal administration to horses with heaves. J Vet Pharmacol Ther. 2008 Dec;31(6):501-10. doi: 10.1111/j.1365-2885.2008.00984.x. PMID: 19000271. 2: Camargo FC, Robinson NE, Berney C, Eberhart S, Baker S, Detolve P, Derksen FJ, Lehner AF, Hughes C, Tobin T. Trimetoquinol: bronchodilator effects in horses with heaves following aerosolised and oral administration. Equine Vet J. 2007 May;39(3):215-20. doi: 10.2746/042516407x173334. PMID: 17520971. 3: Camargo FC, Robinson NE, Berney C, Eberhart S, Baker S, DeTolve P, Derksen FJ, Harkins JD, Lehner AF, Tobin T. Intravenous and intratracheal administration of trimetoquinol, a fast-acting short-lived bronchodilator in horses with 'heaves'. Equine Vet J. 2006 Nov;38(6):563-9. doi: 10.2746/042516406x153355. PMID: 17124848. 4: Konkar AA, Nikulin VI, De Los Angeles J, Hong SS, Fertel RH, Miller DD, Feller DR. Biochemical activities of trimetoquinol analogs at human beta(1)- and beta(3)-adrenergic receptors. Pharmacology. 2001 Jan;62(1):45-55. doi: 10.1159/000056071. PMID: 11150922. 5: Mehta RC, Salazar-Bookaman MM, Fertel RH, De Los Angeles J, Nikulin VI, Fraundorfer PF, Miller DD, Feller DR. Biochemical and functional characterization of 1-benzyl substituted trimetoquinol affinity analogs on rat and human beta-adrenoceptors. Biochem Pharmacol. 2000 Mar 1;59(5):517-29. doi: 10.1016/s0006-2952(99)00376-7. PMID: 10660118. 6: Konkar AA, Vansal SS, Shams G, Fraundorfer PF, Zheng WP, Nikulin VI, De Los Angeles J, Fertel RH, Miller DD, Feller DR. Beta-adrenoceptor subtype activities of trimetoquinol derivatives: biochemical studies on human beta-adrenoceptors expressed in chinese hamster ovary cells. J Pharmacol Exp Ther. 1999 Nov;291(2):875-83. PMID: 10525112. 7: Kumar R, Singh P. Quantitative structure-activity relationship study of iodinated analogues of trimetoquinol as highly potent beta 2-adrenoceptor ligands. Indian J Biochem Biophys. 1998 Dec;35(6):390-2. PMID: 10412236. 8: Shams G, Romstedt KJ, Lust LA, Clark MT, Miller DD, Feller DR. Beta- adrenergic receptor and platelet inhibitory activities of a new series of trimetoquinol and related benzazepine analogs. Gen Pharmacol. 1997 Feb;28(2):323-30. doi: 10.1016/s0306-3623(96)00223-6. PMID: 9013212. 9: Christoff JJ, Bradley L, Miller DD, Lei L, Rodriguez F, Fraundorfer P, Romstedt K, Shams G, Feller DR. Synthesis and evaluation of trimetoquinol derivatives: novel thromboxane A2/prostaglandin H2 antagonists with diminished beta-adrenergic agonist activity. J Med Chem. 1997 Jan 3;40(1):85-91. doi: 10.1021/jm950896w. PMID: 9016331. 10: De Los Angeles JE, Nikulin VI, Shams G, Konkar AA, Mehta R, Feller DR, Miller DD. Iodinated analogs of trimetoquinol as highly potent and selective beta 2-adrenoceptor ligands. J Med Chem. 1996 Sep 13;39(19):3701-11. doi: 10.1021/jm960208o. PMID: 8809159. 11: Konkar AA, Fraundorfer PF, Fertel RH, Burkman AM, Miller DD, Feller DR. Pharmacological activities of trimetoquinol and 1-benzyl halogen-substituted analogues on rat beta-adrenoceptor subtypes. Eur J Pharmacol. 1996 Jun 3;305(1-3):63-71. doi: 10.1016/0014-2999(96)00034-9. PMID: 8813533. 12: Fraundorfer PF, Fertel RH, Miller DD, Feller DR. Biochemical and pharmacological characterization of high-affinity trimetoquinol analogs on guinea pig and human beta adrenergic receptor subtypes: evidence for partial agonism. J Pharmacol Exp Ther. 1994 Aug;270(2):665-74. PMID: 7915318. 13: Fraundorfer PF, Lezama EJ, Salazar-Bookaman MM, Fertel RH, Miller DD, Feller DR. Isomeric-activity ratios of trimetoquinol enantiomers on beta-adrenergic receptor subtypes: functional and biochemical studies. Chirality. 1994;6(2):76-85. doi: 10.1002/chir.530060207. PMID: 7911313. 14: Romstedt KJ, Shin Y, Shams G, Doyle K, Tantishaiyakul V, Clark MT, Adejare A, Hamada A, Miller DD, Feller DR. Halogen-substituted trimetoquinol analogs as thromboxane A2 receptor antagonists in platelets and aorta. Biochem Pharmacol. 1993 Dec 3;46(11):2051-9. doi: 10.1016/0006-2952(93)90647-f. PMID: 8267653. 15: Shin Y, Romstedt KJ, Miller DD, Feller DR. Interactions of nonprostanoid trimetoquinol analogs with thromboxane A2/prostaglandin H2 receptors in human platelets, rat vascular endothelial cells and rat vascular smooth muscle cells. J Pharmacol Exp Ther. 1993 Dec;267(3):1017-23. PMID: 7903383. 16: Markovich KM, Tantishaiyakul V, Hamada A, Miller DD, Romstedt KJ, Shams G, Shin Y, Fraundorfer PF, Doyle K, Feller DR. Synthesis of halogenated trimetoquinol derivatives and evaluation of their beta-agonist and thromboxane A2 (TXA2) antagonist activities. J Med Chem. 1992 Feb 7;35(3):466-79. doi: 10.1021/jm00081a007. PMID: 1346651. 17: Shin Y, Romstedt KJ, Doyle K, Harrold MW, Gerhardt MA, Miller DD, Patil PN, Feller DR. Pharmacologic antagonism of thromboxane A2 receptors by trimetoquinol analogs in vitro and in vivo. Chirality. 1991;3(2):112-7. doi: 10.1002/chir.530030206. PMID: 1830752. 18: Shams G, Fedyna J, Romstedt KJ, Adejare A, Miller DD, Roche VF, Feller DR. Pharmacological properties of novel bicyclic isoquinoline analogs in isolated guinea pig atria, trachea and in human platelets: relationship to trimetoquinol. Gen Pharmacol. 1991;22(6):1155-63. doi: 10.1016/0306-3623(91)90595-w. PMID: 1687397. 19: Nishi H, Fukuyama T, Matsuo M, Terabe S. Chiral separation of diltiazem, trimetoquinol and related compounds by micellar electrokinetic chromatography with bile salts. J Chromatogr. 1990 Aug 31;515:233-43. doi: 10.1016/s0021-9673(01)89318-3. PMID: 2283364. 20: Shams G, Harrold MW, Grazyl B, Miller DD, Feller DR. Pharmacological evaluation of the beta-adrenoceptor agonist properties of N-benzyl substituted trimetoquinol analogues. Eur J Pharmacol. 1990 Aug 10;184(2-3):251-6. doi: 10.1016/0014-2999(90)90616-e. PMID: 1981872. 21: Shams G, Romstedt KJ, Gerhardt MA, Harrold MW, Miller DD, Feller DR. Pharmacological evaluation of the beta-adrenoceptor agonist and thromboxane receptor blocking properties of 1-benzyl substituted trimetoquinol analogues. Eur J Pharmacol. 1990 Aug 2;184(1):21-31. doi: 10.1016/0014-2999(90)90663-q. PMID: 1976530. 22: Ahn CH, Romstedt KJ, Wallace LJ, Miller DD, Feller DR. Characterization of the inhibition of U46619-mediated human platelet activation by the trimetoquinol isomers. Evidence for endoperoxide/thromboxane A2 receptor blockade. Biochem Pharmacol. 1988 Aug 1;37(15):3023-33. doi: 10.1016/0006-2952(88)90292-4. PMID: 3134894. 23: Ahn CH, Wallace LJ, Miller DD, Feller DR. Use of [3H]trimetoquinol as a radioligand in human platelets: interaction with putative endoperoxide/thromboxane A2 receptor sites. Thromb Res. 1988 May 1;50(3):387-99. doi: 10.1016/0049-3848(88)90268-x. PMID: 2969151. 24: Fedyna JS, Adejare A, Miller DD, Feller DR. Pharmacological evaluation of the beta-adrenoceptor agonist and thromboxane antagonist properties of N-substituted trimetoquinol analogues. Eur J Pharmacol. 1987 Mar 17;135(2):161-71. doi: 10.1016/0014-2999(87)90608-x. PMID: 2884118. 25: Harrold MW, Gerhardt MA, Romstedt K, Feller DR, Miller DD. Synthesis and platelet antiaggregatory activity of trimetoquinol analogs as endoperoxide/thromboxane A2 antagonists. Drug Des Deliv. 1987 Feb;1(3):193-207. PMID: 3509333. 26: Adejare A, Miller DD, Fedyna JS, Ahn CH, Feller DR. Syntheses and beta- adrenergic agonist and antiaggregatory properties of N-substituted trimetoquinol analogues. J Med Chem. 1986 Sep;29(9):1603-9. doi: 10.1021/jm00159a008. PMID: 2875182. 27: Mukhopadhyay A, Miller DD, Feller DR. Antiallergic effect of trimetoquinol analogs on actively sensitized guinea pig lung tissue, in vitro. Biochem Pharmacol. 1986 Sep 1;35(17):2977-9. doi: 10.1016/0006-2952(86)90497-1. PMID: 2427089. 28: Clark MT, Chang J, Navran SS, Huzoor-Akbar, Mukhopadhyay A, Amin H, Feller DR, Miller DD. Synthesis and investigation of the beta-adrenoceptor agonist and platelet antiaggregatory properties of 1,7,8-trisubstituted 2,3,4,5-tetrahydro-1H-2-benzazepine analogues of trimetoquinol. J Med Chem. 1986 Feb;29(2):181-5. doi: 10.1021/jm00152a003. PMID: 2869145. 29: Babich M, Atkinson J, Piascik MT. The effects of trimetoquinol on the intact rabbit heart and myocardial adenylate cyclase activity: evidence for spare myocardial beta receptors. J Mol Cell Cardiol. 1985 Jun;17(6):565-74. doi: 10.1016/s0022-2828(85)80025-0. PMID: 2991540. 30: Mukhopadhyay A, Navran SS, Amin HM, Abdel-Aziz SA, Chang J, Sober DJ, Miller DD, Feller DR. Effect of trimetoquinol analogs for antagonism of endoperoxide/thromboxane A2-mediated responses in human platelets and rat aorta. J Pharmacol Exp Ther. 1985 Jan;232(1):1-9. PMID: 3855323. 31: Mayo JR, Miller DD, Feller DR. Stereoselective inhibition of prostaglandin- induced calcium release from platelet membranes by trimetoquinol. Biochem Pharmacol. 1983 Jun 15;32(12):1952-5. doi: 10.1016/0006-2952(83)90066-7. PMID: 6882470. 32: Williams DA, Maher TJ, Zaveri DC. Identification of a tetrahydroprotoberberine as a metabolite of trimetoquinol in the rat. Biochem Pharmacol. 1983 Apr 15;32(8):1447-8. doi: 10.1016/0006-2952(83)90461-6. PMID: 6860364. 33: Suzuki T, Tsuzurahara K, Murata T, Takeyama S. Quantitative determination of trimetoquinol in plasma as its mixed pentafluoropropionyl-trimethylsilyl derivative by gas chromatography mass spectrometry. Biomed Mass Spectrom. 1982 Mar;9(3):94-8. doi: 10.1002/bms.1200090303. PMID: 7066482. 34: Akbar H, Navran SS, Miller DD, Feller DR. Antiplatelet actions of trimetoquinol isomers: evidence for inhibition of a prostaglandin-independent pathway of platelet aggregation. Biochem Pharmacol. 1982 Mar 1;31(5):886-9. doi: 10.1016/0006-2952(82)90482-8. PMID: 6123325. 35: Mukhopadhyay A, Sober DJ, Chang J, Slenn RT, Amin HM, Miller DD, Feller DR. Bronchoselective actions of a new series of trimetoquinol analogues. Eur J Pharmacol. 1982 Feb 5;77(4):209-19. doi: 10.1016/0014-2999(82)90121-2. PMID: 6277666. 36: Gwee MC. A pharmacological evaluation of the potential of a bronchodilator trimetoquinol to produce tachycardia and skeletal muscle tremor. Singapore Med J. 1981 Oct;22(5):250-3. PMID: 7344085. 37: Yamada K, Takeda M, Itoh N, Ikezawa K, Kiyomoto A, Iwakuma T. Studies on 1,2,3,4-tetrahydroisoquinolines. III. 1) Syntheses and beta-adrenoceptor activities of methyl derivatives of trimetoquinol. Chem Pharm Bull (Tokyo). 1981 Oct;29(10):2816-24. doi: 10.1248/cpb.29.2816. PMID: 6119163. 38: Mayo JR, Navran SS, Huzoor-Akbar, Miller DD, Feller DR. Stereo-dependent inhibition of human platelet function by the optical isomers of trimetoquinol. Biochem Pharmacol. 1981 Aug 15;30(16):2237-41. doi: 10.1016/0006-2952(81)90093-9. PMID: 7188564. 39: Sober DJ, Chang J, Fowble JW, Mukhopadhyay A, Feller DR, Miller DD, Fairchild EH. Selective and potent beta 2-adrenoceptor agents within the tetrahydroisoquinoline class: effect of methyl substitution at the benzylic carbon of the 1-(3,4,5-trimethoxybenzyl) group of trimetoquinol. J Med Chem. 1981 Aug;24(8):970-4. doi: 10.1021/jm00140a011. PMID: 6120236. 40: Yamada K, Ikezaki M, Umino N, Ohtsuka H, Itoh N, Ikezawa K, Kiyomoto A, Iwakuma T. Studies on 1,2,3,4-tetrahydroisoquinoline derivatives. I. Syntheses and beta-adrenoceptor activities of positional isomers of trimetoquinol with respect to its 6,7-dihydroxyl groups. Chem Pharm Bull (Tokyo). 1981 Mar;29(3):744-53. doi: 10.1248/cpb.29.744. PMID: 6113898.