Thiomethoxyflurane

Thiomethoxyflurane

Identifiers
IUPAC name 2,2-dichloro-1,1-difluoro-1-methylsulfanylethane
CAS Number	2045-53-6
PubChem CID	164920
ChemSpider	144586
CompTox Dashboard (EPA)	DTXSID80174410
Chemical and physical data
Formula	C3H4Cl2F2S
Molar mass	181.02 g·mol−1
3D model (JSmol)	Interactive image
SMILES CSC(C(Cl)Cl)(F)F
InChI InChI=1S/C3H4Cl2F2S/c1-8-3(6,7)2(4)5/h2H,1H3 Key:BJMNUMOCQIVWFA-UHFFFAOYSA-N

Thiomethoxyflurane, is a volatile, inhalational anesthetic. It is an analogue of the widely used inhalational anesthetic methoxyflurane but with the methoxy group replaced by a heavier methylthio group. Thiomethoxyflurane is approximately 7.5x more potent than methoxyflurane, making it the most potent inhalational anesthetic ever discovered, but was never developed for medical use due to its lower volatility, higher toxicity, and longer duration of action compared to methoxyflurane. However, its high potency has made it useful for research into the mechanism of action of volatile anesthetics and identifying the receptor targets at which they act. ^{[1] [2] [3] [4] [5]}

References

1. Tanifuji Y, Eger EI, Terrell RC (1977). "Some characteristics of an exceptionally potent inhaled anesthetic: thiomethoxyflurane". Anesthesia and Analgesia. 56 (3): 387–390. doi:10.1213/00000539-197705000-00014. PMID   559438.
2. Firestone LL, Sauter JF, Braswell LM, Miller KW (June 1986). "Actions of general anesthetics on acetylcholine receptor-rich membranes from Torpedo californica". Anesthesiology. 64 (6): 694–702. doi:10.1097/00000542-198606000-00004. PMID   3717633.
3. Morgan PG, Sedensky MM, Meneely PM, Cascorbi HF (August 1988). "The effect of two genes on anesthetic response in the nematode Caenorhabditis elegans". Anesthesiology. 69 (2): 246–251. doi:10.1097/00000542-198808000-00015. PMID   2900611.
4. Morgan PG, Sedensky M, Meneely PM (April 1990). "Multiple sites of action of volatile anesthetics in Caenorhabditis elegans". Proceedings of the National Academy of Sciences of the United States of America. 87 (8): 2965–2969. Bibcode:1990PNAS...87.2965M. doi: 10.1073/pnas.87.8.2965 . PMC   53814 . PMID   2326259.
5. Menon DK (September 1993). "Additional evidence against a unitary site of volatile anesthetic action". Anesthesia and Analgesia. 77 (3): 645. doi:10.1213/00000539-199309000-00050. PMID   8368576.