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MedKoo Cat#: 585272 | Name: Trecadrine

Description:

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

Trecadrine is a beta 3-adrenergic agonist that inhibits galactose intestinal absorption.

Chemical Structure

Trecadrine
Trecadrine
CAS#90845-56-0

Theoretical Analysis

MedKoo Cat#: 585272

Name: Trecadrine

CAS#: 90845-56-0

Chemical Formula: C27H29NO

Exact Mass: 383.2249

Molecular Weight: 383.54

Elemental Analysis: C, 84.55; H, 7.62; N, 3.65; O, 4.17

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 #
No Data
Synonym
Trecadrine
IUPAC/Chemical Name
(1R,2S)-alpha-(1-((2-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)ethyl)methylamino)ethyl)benzyl alcohol
InChi Key
BHVGOYREXHCFOE-ACVCQEAVSA-N
InChi Code
InChI=1S/C27H29NO/c1-20(27(29)23-12-4-3-5-13-23)28(2)19-18-26-24-14-8-6-10-21(24)16-17-22-11-7-9-15-25(22)26/h3-15,18,20,27,29H,16-17,19H2,1-2H3/t20-,27?/m1/s1
SMILES Code
C[C@H](C(O)C1=CC=CC=C1)N(C/C=C2C3=CC=CC=C3CCC4=CC=CC=C/24)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 383.54 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: Diez-Sampedro A, Milagro FI, Berraondo B, Zulet MA, Martinez JA, Barber A. Effects of trecadrine, a beta 3-adrenergic agonist, on intestinal absorption of D-galactose and disaccharidase activities in three physiopathological models. J Pharm Pharmacol. 1997 Sep;49(9):873-7. PubMed PMID: 9306254. 2: Moreno-Aliaga MJ, Martínez JA, Stanhope KL, Fernández-Otero MP, Havel PJ. Effects of Trecadrine, a beta3-adrenergic agonist, on leptin secretion, glucose and lipid metabolism in isolated rat adipocytes. Int J Obes Relat Metab Disord. 2002 Jul;26(7):912-9. PubMed PMID: 12080443. 3: Milagro FI, Martínez JA. Effects of the oral administration of a beta3-adrenergic agonist on lipid metabolism in alloxan-diabetic rats. J Pharm Pharmacol. 2000 Jul;52(7):851-6. PubMed PMID: 10933136. 4: Berraondo B, Martínez JA. Free fatty acids are involved in the inverse relationship between hormone-sensitive lipase (HSL) activity and expression in adipose tissue after high-fat feeding or beta3-adrenergic stimulation. Obes Res. 2000 May;8(3):255-61. PubMed PMID: 10832769. 5: Milagro FI, Gómez-Ambrosi J, Forga L, Martínez JA. A beta3-adrenergic agonist increases muscle GLUT1/GLUT4 ratio, and regulates liver glucose utilization in diabetic rats. Diabetes Obes Metab. 1999 Mar;1(2):97-104. PubMed PMID: 11220517. 6: Gómez-Ambrosi J, Frühbeck G, Aguado M, Milagro FI, Margareto J, Martínez AJ. Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats. Int J Mol Med. 2001 Jul;8(1):103-9. PubMed PMID: 11408957. 7: Moreno-Aliaga MJ, Lamas O, Marti A, Martínez JA. Effects of a beta3-adrenergic agonist on glucose uptake and leptin expression and secretion in cultured adipocytes from lean and overweight (cafeteria) rats. Biochem Biophys Res Commun. 2002 Mar 15;291(5):1201-7. PubMed PMID: 11883944. 8: Berraondo B, Marti A, Duncan JS, Trayhurn P, Martínez JA. Up-regulation of muscle UCP2 gene expression by a new beta3-adrenoceptor agonist, trecadrine, in obese (cafeteria) rodents, but down-regulation in lean animals. Int J Obes Relat Metab Disord. 2000 Feb;24(2):156-63. PubMed PMID: 10702765. 9: Zulet MA, Berraondo B, Milagro FI, Martínez JA. Hypolipidemic properties of a diphenyl-methylen-ethylamine derivative with affinity for beta 3-adrenoceptors in a model of hypercholesterolemia. Farmaco. 1999 Oct 30;54(10):710-2. PubMed PMID: 10575741. 10: Gómez-Ambrosi J, Frühbeck G, Martínez JA. Interactions between an alpha2-adrenergic antagonist and a beta3-adrenergic agonist on the expression of UCP2 and UCP3 in rats. J Physiol Biochem. 2002 Mar;58(1):17-23. PubMed PMID: 12222743. 11: Lamas O, Martínez JA, Marti A. Effects of a beta3-adrenergic agonist on the immune response in diet-induced (cafeteria) obese animals. J Physiol Biochem. 2003 Sep;59(3):183-91. PubMed PMID: 15000449. 12: Gómez-Ambrosi J, Frühbeck G, Martínez JA. Rapid in vivo PGC-1 mRNA upregulation in brown adipose tissue of Wistar rats by a beta(3)-adrenergic agonist and lack of effect of leptin. Mol Cell Endocrinol. 2001 May 15;176(1-2):85-90. PubMed PMID: 11369446. 13: Díez-Sampedro A, Pérez M, Cobo MT, Martínez JA, Barber A. Effect of different beta-adrenergic agonists on the intestinal absorption of galactose and phenylalanine. J Pharm Pharmacol. 1998 Aug;50(8):907-11. PubMed PMID: 9751456. 14: Berraondo B, Bonafonte A, Fernandez-Otero MP, Martinez JA. Effects on energy utilization of a beta3-adrenergic agonist in rats fed on a cafeteria diet. Eat Weight Disord. 1997 Sep;2(3):130-7. PubMed PMID: 14655836. 15: Milagro FI, Gómez-Ambrosi J, Martínez-Ansó E, Martínez JA. Effect of a beta3-adrenergic agonist on liver glucokinase gene expression in alloxan-diabetic rats. J Physiol Biochem. 1999 Mar;55(1):25-31. PubMed PMID: 10494657. 16: Barrionuevo M, Milagro FI, Cenarruzabeitia E, Martínez JA. Potential anti-diabetic applications of a new molecule with affinity for beta 3-adrenoceptors. Life Sci. 1996;59(11):PL141-6. PubMed PMID: 8795708. 17: Gómez-Ambrosi J, Frühbeck G, Martínez JA. Leptin, but not a beta 3-adrenergic agonist, upregulates muscle uncoupling protein-3 messenger RNA expression: short-term thermogenic interactions. Cell Mol Life Sci. 1999 Jun;55(6-7):992-7. PubMed PMID: 10412376.