Thiamylal

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

MedKoo CAT#: 318859

CAS#: 77-27-0

Description: Thiamylal (Surital) is a barbiturate derivative invented in the 1950s. It has sedative, anticonvulsant, and hypnotic effects, and is used as a strong but short acting sedative. Thiamylal is still in current use, primarily for induction in surgical anaesthesia or as an anticonvulsant to counteract side effects from other anaesthetics. It is the thiobarbiturate analogue of secobarbital. Thiamylal is discontinued.


Chemical Structure

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Thiamylal
CAS# 77-27-0

Theoretical Analysis

MedKoo Cat#: 318859
Name: Thiamylal
CAS#: 77-27-0
Chemical Formula: C12H18N2O2S
Exact Mass: 254.1089
Molecular Weight: 254.348
Elemental Analysis: C, 56.67; H, 7.13; N, 11.01; O, 12.58; S, 12.60

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Pricing updated 2021-02-27. Prices are subject to change without notice.

Thiamylal is discontinued. (DEA controlled substance.)

Synonym: Thiamylal; Thioseconal; Surital; Thioquinalbarbitone.

IUPAC/Chemical Name: 5-pentan-2-yl-5-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione

InChi Key: XLOMZPUITCYLMJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

SMILES Code: O=C(C1(C(CCC)C)CC=C)NC(NC1=O)=S

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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 254.348 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Wu RS, Yu CS, Liu KC, Huang HY, Ip SW, Lin JP, Chueh FS, Yang JS, Chung JG. Citosol (thiamylal sodium) triggers apoptosis and affects gene expressions of murine leukemia RAW 264.7 cells. Hum Exp Toxicol. 2012 Aug;31(8):771-9. doi: 10.1177/0960327111429137. PubMed PMID: 22895347.

2: Higashijima U, Terao Y, Ichinomiya T, Miura K, Fukusaki M, Sumikawa K. A comparison of the effect on QT interval between thiamylal and propofol during anaesthetic induction*. Anaesthesia. 2010 Jul;65(7):679-83. doi: 10.1111/j.1365-2044.2010.06341.x. Epub 2010 May 28. PubMed PMID: 20528837.

3: Lin CK, Lau YW, Chan HM, Wang FY, Lin TJ, Cheng KI, Feng YT, Hung CL. Intravenous thiamylal and local anesthetic infiltration for pediatric facial repair procedures performed in emergency departments. Kaohsiung J Med Sci. 2010 Apr;26(4):192-9. doi: 10.1016/S1607-551X(10)70028-0. PubMed PMID: 20434100.

4: Hidaka I, Kurokawa H, Yasuda T, Hamada H, Kawamoto M, Yuge O. Thiamylal and thiopental attenuate beta-adrenergic signaling pathway by suppressing adenylyl cyclase in rat ventricular myocytes. Hiroshima J Med Sci. 2009 Mar;58(1):9-15. PubMed PMID: 19400552.

5: Tanaka E, Tobita T, Murai Y, Okabe Y, Yamada A, Kano T, Higashi H, Shimoji K. Thiamylal antagonizes the inhibitory effects of dorsal column stimulation on dorsal horn activities in humans. Neurosci Res. 2009 Aug;64(4):391-6. doi: 10.1016/j.neures.2009.04.012. Epub 2009 Apr 23. PubMed PMID: 19393696.

6: Hsieh MY, Hung GY, Hsieh YL, Chang CY, Hwang B. Deep sedation with methohexital or thiamylal with midazolam for invasive procedures in children with acute lymphoblastic leukemia. Acta Paediatr Taiwan. 2005 Sep-Oct;46(5):294-300. PubMed PMID: 16640004.

7: Iwata S, Okumura A, Kato T, Itomi K, Kuno K. Efficacy and adverse effects of rectal thiamylal with oral triclofos for children undergoing magnetic resonance imaging. Brain Dev. 2006 Apr;28(3):175-7. Epub 2005 Dec 20. PubMed PMID: 16368209.

8: Atwal OS, McDonell W. In vivo interaction of pulmonary intravascular macrophages with activated platelets in microvessels of equine lung after multiple exposures to halothane, isoflurane, and thiamylal: a comparative ultrastructural and cytochemical study. Anat Rec A Discov Mol Cell Evol Biol. 2005 Jun;284(2):574-84. PubMed PMID: 15880489.

9: Eguchi S, Kawano T, Oshita S, Nakajo N. [Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. Masui. 2005 Apr;54(4):364-9. Japanese. PubMed PMID: 15852621.

10: Tomari S, Matsuse H, Ootsubo T, Miyazaki Y, Kohno S. [A survival case of tetanus complicated with disseminated intravascular coagulation syndrome in the elderly, rescued by mechanical ventilation and administration of thiamylal]. Kansenshogaku Zasshi. 2005 Jan;79(1):25-8. Japanese. PubMed PMID: 15717480.

11: Yoshida M, Akane A, Nishikawa M, Watabiki T, Tsuchihashi H. Extraction of thiamylal in serum using hydrophilic acetonitrile with subzero-temperature and salting-out methods. Anal Chem. 2004 Aug 15;76(16):4672-5. PubMed PMID: 15307775.

12: Kawano T, Oshita S, Takahashi A, Tsutsumi Y, Tomiyama Y, Kitahata H, Kuroda Y, Nakaya Y. Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. Anesthesiology. 2004 Feb;100(2):338-46. PubMed PMID: 14739809.

13: Sato M, Hirakata H, Nakagawa T, Arai K, Fukuda K. Thiamylal and pentobarbital have opposite effects on human platelet aggregation in vitro. Anesth Analg. 2003 Nov;97(5):1353-9. PubMed PMID: 14570651.

14: Yamaura K, Hoka S, Okamoto H, Kandabashi T, Akiyoshi K, Takahashi S. Changes in left ventricular end-diastolic area, end-systolic wall stress, and fractional area change during anesthetic induction with propofol or thiamylal. J Anesth. 2000;14(3):138-42. PubMed PMID: 14564580.

15: Wajima Z, Shiga T, Yoshikawa T, Ogura A, Imanaga K, Inoue T, Ogawa R. Intravenous alprostadil, an analog of prostaglandin E1, prevents thiamylal-fentanyl-induced bronchoconstriction in humans. Anesth Analg. 2003 Aug;97(2):456-60, table of contents. PubMed PMID: 12873934.

16: Shiga Y, Minami K, Uezono Y, Segawa K, Nagaoka E, Shiraishi M, Noguchi T, Shigematsu A. Effects of the intravenously administered anaesthetics ketamine, propofol, and thiamylal on the cortical renal blood flow in rats. Pharmacology. 2003 May;68(1):17-23. PubMed PMID: 12660475.

17: Wajima Z, Yoshikawa T, Ogura A, Imanaga K, Shiga T, Inoue T, Ogawa R. Intravenous nicorandil prevents thiamylal-fentanyl-induced bronchoconstriction in humans. Crit Care Med. 2003 Feb;31(2):485-90. PubMed PMID: 12576956.

18: Fukui K, Morioka T, Hisada K, Nishio S, Irita K, Takahashi S. Effects of thiamylal, sevoflurane and isoflurane on the cortically recorded somatosensory evoked potentials. Eur J Anaesthesiol. 2002 Dec;19(12):899-901. PubMed PMID: 12510912.

19: Wajima Z, Yoshikawa T, Ogura A, Imanaga K, Shiga T, Inoue T, Ogawa R. Intravenous colforsin daropate, a water-soluble forskolin derivative, prevents thiamylal-fentanyl-induced bronchoconstriction in humans. Crit Care Med. 2002 Apr;30(4):820-6. PubMed PMID: 11940752.

20: Sugimura M, Kitayama S, Morita K, Imai Y, Irifune M, Takarada T, Kawahara M, Dohi T. Effects of GABAergic agents on anesthesia induced by halothane, isoflurane, and thiamylal in mice. Pharmacol Biochem Behav. 2002 May;72(1-2):111-6. PubMed PMID: 11900777.