Tybamate

• CAT Number: I037649
• CAS Number: 4268-36-4
• Molecular Formula: C13H26N2O4
• Molecular Weight: 274.361
• Purity: 98%
• Synonyms: Tybamate; W 713; W-713; W713; NSC 172126; Solacen, Tybatran, Effisax
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Carbamic acid, butyl-, 2-(((aminocarbonyl)oxy)methyl)-2-methylpentyl ester
• InChI: InChI=1S/C13H26N2O4/c1-4-6-8-15-12(17)19-10-13(3,7-5-2)9-18-11(14)16/h4-10H2,1-3H3,(H2,14,16)(H,15,17)
• InChIKey: PRBORDFJHHAISJ-UHFFFAOYSA-N
• SMILES: O=C(OCC(C)(COC(N)=O)CCC)NCCCC

Tybamate (Cat.No:I037649) is discontinued (DEA controlled substance). is an anxiolytic of the carbamate family. It is a prodrug for meprobamate in the same way as the better known drug carisoprodol. It has liver enzyme inducing effects similar to those of phenobarbital but much weaker.

Reference

1: Segelman FH, Kelton E, Terzi RM, Kucharczyk N, Sofia RD. The comparative potency of phenobarbital and five 1,3-propanediol dicarbamates for hepatic cytochrome P450 induction in rats. Res Commun Chem Pathol Pharmacol. 1985 Jun;48(3):467-70. PubMed PMID: 4023427.
2: Lehmann E. [Internal and external stress and tybamate and secobarbital: an experimental investigation of their interactions (author’s transl)]. Arzneimittelforschung. 1976;26(6):1132-3. German. PubMed PMID: 989399.
3: Bradley SG, Rose WC. Enhanced toxicity for mice of pactamycin with bacterial endotoxin. Antimicrob Agents Chemother. 1973 Jun;3(6):686-92. PubMed PMID: 4790618; PubMed Central PMCID: PMC444481.
4: Kirsten EB, Tseng TC. Effects of tybamate and pentylenetetrazol on spinal interneurons. Experientia. 1972 Dec 15;28(12):1459-60. PubMed PMID: 4654212.
5: Cremoncini C, Liuzzi A. [Tybamate, recently synthetized anxiolytic agent, in the treatment of emotional and neurovegetative symptoms of hyperthyroidism. Clinico-statistical study]. Minerva Med. 1972 Jan 24;63(5):296-307. Italian. PubMed PMID: 5012345.
6: Tseng TC, Wang SC. Locus of action of centrally acting muscle relaxants, diazepam and tybamate. J Pharmacol Exp Ther. 1971 Aug;178(2):350-60. PubMed PMID: 5570459.
7: Serafetinides EA, Clark ML. Effects of Tybamate in chronic schizophrenia. (Minor tranquilizers as adjunct therapy in psychosis). Dis Nerv Syst. 1971 Aug;32(8):567-71. PubMed PMID: 5094163.
8: Hesbacher P, Zamostien BB, Kelly EA, Jenkins BW, Rickels K. Tybamate in treatment resistant headaches. Headache. 1971 Jan;10(4):148-9. PubMed PMID: 5543640.
9: Tseng TC, Przybyla AC, Chen ST, Wang SC. Locus of central depressant action of tybamate. Neuropharmacology. 1970 May;9(3):211-8. PubMed PMID: 5268924.
10: DiMascio A, Gardos G, Harmatz J, Shader R. Tybamate: an examination of its actions in “high” and “low” anxious normals. Dis Nerv Syst. 1969 Nov;30(11):758-63. PubMed PMID: 4391128.
11: Majeron MA, Toselli E. [Clinical experience with a new tranquilizing agent: tybamate]. Riv Sper Freniatr Med Leg Alien Ment. 1969 Oct 31;93(5):1226-40. Italian. PubMed PMID: 5407446.
12: Pennington VM. Evaluation of tybamate in mental disorders. Behav Neuropsychiatry. 1969 Sep;1(6):7-10. PubMed PMID: 5393016.
13: Denber HC, Roland M. Effect of tybamate on psychosomatic symptoms in a group of infertility patients. A double-blind study. Fertil Steril. 1969 May-Jun;20(3):373-9. PubMed PMID: 4890013.
14: Douglas JF, Smith NB, Stockage JA. Gas chromatographic determination of mebutamate, carisoprodol, and tybamate in plasma and urine. J Pharm Sci. 1969 Jan;58(1):145-6. PubMed PMID: 5765828.
15: Myers RD, Cicero TJ. Effects of tybamate on ethanol intake in rats during psychological stress in an avoidance task. Arch Int Pharmacodyn Ther. 1968 Oct;175(2):440-6. PubMed PMID: 5750456.
16: Rickels K, Hesbacher P, Vandervort W, Phillips F, Hutchison J, Sablosky L, Lavan D. Tybamate–a perplexing drug. Am J Psychiatry. 1968 Sep;125(3):76-82. PubMed PMID: 4875386.
17: Turns D, Denber HC, Turns CN. [Unexpected therapeutic effects of tybamate in psychoses]. Ann Med Psychol (Paris). 1968 Jul;2(2):216-20. French. PubMed PMID: 5684178.
18: Meshel E, Denber HC. The use of tybamate in psychotic patients. (A further double blind study). Dis Nerv Syst. 1968 Apr;29(4):243-5. PubMed PMID: 4870945.
19: Hollister LE, Clyde DJ. Blood levels of pentobarbital sodium, meprobamate, and tybamate in relation to clinical effects. Clin Pharmacol Ther. 1968 Mar-Apr;9(2):204-8. PubMed PMID: 4867871.
20: Solaro F, Corletto F. [Tybamate in the practice at geriatric outpatient clinics]. G Gerontol. 1968 Jan;16(1):57-66. Italian. PubMed PMID: 5713039.