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MedKoo Cat#: 573660 | Name: Trimeprazine, (R)-

Description:

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

Trimeprazine is a phenothiazine derivative that is used as an antipruritic (it prevents itching from causes such as eczema or poison ivy, by acting as an antihistamine). It also acts as a sedative, hypnotic, and antiemetic for prevention of motion sickness. Although it is structurally related to drugs such as chlorpromazine, it is not used as an antipsychotic.

Chemical Structure

Trimeprazine, (R)-
Trimeprazine, (R)-
CAS#2256-27-1 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 573660

Name: Trimeprazine, (R)-

CAS#: 2256-27-1 (R-isomer)

Chemical Formula: C18H22N2S

Exact Mass: 298.1504

Molecular Weight: 298.45

Elemental Analysis: C, 72.44; H, 7.43; N, 9.39; S, 10.74

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 #
1936-51-2 (HCl) 84-96-8 (free base) 179167-82-9 (maleate) 4330-99-8 (Tartrate) 36506-71-5 (R-isomer maleate) 179463-08-2 (S-isomer maleate) 2256-27-1 (R-isomer)
Synonym
(-)-Alimemazine, (-)-Trimeprazine, Alimemazine, (R)-; Trimeprazine, (R)-
IUPAC/Chemical Name
10H-Phenothiazine-10-propanamine, N,N,beta-trimethyl-, (R)-
InChi Key
ZZHLYYDVIOPZBE-CQSZACIVSA-N
InChi Code
1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3/t14-/m1/s1
SMILES Code
C[C@H](CN(C)C)CN1c2ccccc2Sc3ccccc13
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 298.45 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: Escuder-Gilabert L, Martín-Biosca Y, Perez-Baeza M, Sagrado S, Medina- Hernández MJ. Trimeprazine is enantioselectively degraded by an activated sludge in ready biodegradability test conditions. Water Res. 2018 Sep 15;141:57-64. doi: 10.1016/j.watres.2018.05.008. Epub 2018 May 9. PMID: 29775773. 2: Kuznetsova A, Yu Y, Hollister-Lock J, Opare-Addo L, Rozzo A, Sadagurski M, Norquay L, Reed JE, El Khattabi I, Bonner-Weir S, Weir GC, Sharma A, White MF. Trimeprazine increases IRS2 in human islets and promotes pancreatic β cell growth and function in mice. JCI Insight. 2016;1(3):e80749. doi: 10.1172/jci.insight.80749. Epub 2016 Mar 17. PMID: 27152363; PMCID: PMC4854304. 3: Genois A, Haig M, Des Roches A, Sirard A, Le May S, McCuaig CC. Case report of atopic dermatitis with refractory pruritus markedly improved with the novel use of clonidine and trimeprazine. Pediatr Dermatol. 2014 Jan-Feb;31(1):76-9. doi: 10.1111/j.1525-1470.2012.01756.x. Epub 2012 Jul 2. PMID: 22747704. 4: Bello LL. Factors affecting efficacy of oral trimeprazine sedation for dental procedures in children: A retrospective study. Saudi Dent J. 2011 Apr;23(2):87-90. doi: 10.1016/j.sdentj.2011.01.004. Epub 2011 Feb 3. PMID: 23960504; PMCID: PMC3723122. 5: Agrawal K, Wu HF. Drop-to-drop solvent microextraction coupled with gas chromatography/mass spectrometry for rapid determination of trimeprazine in urine and blood of rats: application to pharmacokinetic studies. Rapid Commun Mass Spectrom. 2007;21(20):3352-6. doi: 10.1002/rcm.3221. PMID: 17880040. 6: Kintz P, Villain M, Cirimele V. Determination of trimeprazine-facilitated sedation in children by hair analysis. J Anal Toxicol. 2006 Jul-Aug;30(6):400-2. doi: 10.1093/jat/30.6.400. PMID: 16872573. 7: Schindler R, Fielenbach T, Rave G. A comparative study on the effects of oral amiodarone and trimeprazine, two in vitro retinyl ester hydrolase inhibitors, on the metabolic availability of vitamin A in rats. Br J Nutr. 2005 Nov;94(5):675-83. doi: 10.1079/bjn20051495. PMID: 16277768. 8: Mohammadi R, Gaudoneix-Taieb M, Armand-Branger S, Beauverie P, Poisson N. Place de l'alimémazine parmi les hypnotiques dans un établissement de soins psychiatriques [Value of trimeprazine among hypnotics in a psychiatric facility]. Encephale. 2000 Sep-Oct;26(5):75-80. French. PMID: 11192808. 9: Lutka A, Koziara J. Interaction of trimeprazine with cyclodextrins in aqueous solution. Acta Pol Pharm. 2000 Sep-Oct;57(5):369-74. PMID: 11126028. 10: Guha Thakurta A, Mandal SK, Ganguly K, Dastidar SG, Chakrabarty AN. A new powerful antibacterial synergistic combination of trimethoprim and trimeprazine. Acta Microbiol Immunol Hung. 2000;47(1):21-8. PMID: 10735187. 11: France KG, Blampied NM, Wilkinson P. A multiple-baseline, double-blind evaluation of the effects of trimeprazine tartrate on infant sleep disturbance. Exp Clin Psychopharmacol. 1999 Nov;7(4):502-13. doi: 10.1037//1064-1297.7.4.502. PMID: 10609985. 12: Sauvage MF, Rousseau A, Marquet P, Dumeirain F, Raby C, Lachâtre G. In vitro and in vivo study of the antithyroid side effects of trimeprazine. Toxicol Appl Pharmacol. 1999 Jul 15;158(2):125-31. doi: 10.1006/taap.1999.8699. PMID: 10406927. 13: Roelofse JA, Louw LR, Roelofse PG. A double blind randomized comparison of oral trimeprazine-methadone and ketamine-midazolam for sedation of pediatric dental patients for oral surgical procedures. Anesth Prog. 1998 Winter;45(1):3-11. PMID: 9790003; PMCID: PMC2148942. 14: Mitchell V, Grange C, Black A, Train J. A comparison of midazolam with trimeprazine as an oral premedicant for children. Anaesthesia. 1997 May;52(5):416-21. doi: 10.1111/j.1365-2044.1997.120-az0122.x. PMID: 9165958. 15: Dastidar SG, Jairaj J, Mookerjee M, Chakrabarty AN. Studies on antimicrobial effect of the antihistaminic phenothiazine trimeprazine tartrate. Acta Microbiol Immunol Hung. 1997;44(3):241-7. PMID: 9468728. 16: Patel D, Meakin G. Oral midazolam compared with diazepam-droperidol and trimeprazine as premedicants in children. Paediatr Anaesth. 1997;7(4):287-93. doi: 10.1046/j.1460-9592.1997.d01-88.x. PMID: 9243685. 17: Harling DW. Trimeprazine tartrate and convulsions. Anaesthesia. 1995 Jan;50(1):97-8. doi: 10.1111/j.1365-2044.1995.tb04550.x. PMID: 7702180. 18: Cray SH, Hinton W. Sedation for investigations: prolonged effect of chloral and trimeprazine. Arch Dis Child. 1994 Aug;71(2):179. doi: 10.1136/adc.71.2.179-a. PMID: 7944549; PMCID: PMC1029960. 19: Pérez-Ruiz T, Martínez-Lozano C, Tomás V, Sidrach de Cardona C. Flow- injection fluorimetric determination of trimeprazine and trifluoperazine in pharmaceutical preparations. Talanta. 1993 Sep;40(9):1361-5. doi: 10.1016/0039-9140(93)80211-9. PMID: 18965791. 20: Sultan SM. Computer assisted optimization of a flow-injection method for the assay of promethazine, chlorpromazine and trimeprazine in drug formulations. Talanta. 1993 May;40(5):681-6. doi: 10.1016/0039-9140(93)80278-y. PMID: 18965686.