TL 2636

TL 2636
Identifiers
	IUPAC name α-Cyclohexyl-4,5α-epoxy-3-hydroxy-6-methoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol;
CAS Number	16758-47-7;
PubChem CID	204640;
ChemSpider	177249;
CompTox Dashboard (EPA)	DTXSID70937354 ;
Chemical and physical data
Formula	C28H37NO4
Molar mass	451.607 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC([C@H]1CC23C=C[C@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)C)OC)(C7CCCCC7)O;
	InChI InChI=1S/C28H37NO4/c1-25(31,18-7-5-4-6-8-18)20-16-26-11-12-28(20,32-3)24-27(26)13-14-29(2)21(26)15-17-9-10-19(30)23(33-24)22(17)27/h9-12,18,20-21,24,30-31H,4-8,13-16H2,1-3H3/t20-,21-,24-,25?,26?,27+,28+/m1/s1; Key:SHOLSAOUSMCLOR-HGRVVPQMSA-N;

TL 2636 (M-125) is an opioid drug derived from thebaine, one of the bridged oripavine family of drugs known as the Bentley compounds which includes drugs such as buprenorphine and etorphine. TL 2636 is closely related to etorphine and is a similarly potent opioid analgesic and sedative, but at low doses is characterised by producing pronounced nausea and vomiting, with a long duration of action. It was investigated as a potential incapacitating agent but was not successful due to a poor therapeutic index.^[1]^[2]^[3]^[4]^[5]

References

^ Bentley KW, Hardy DG (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. Bibcode:1967JAChS..89.3281B. doi:10.1021/ja00989a032. PMID 6042764.
^ Callaway S, Hollyhock WM, Ladell WS (1963). An Oripavine Derivative (TL2636) as a Potential Incapacitating Agent. Porton Technical Paper (Report). 835, PRO/WO189/357.
^ Dando M (January 2006). The UK's Search for an Incapacitating ('Non-Lethal') Chemical Agent in the 1960s. Bradford Project on Strengthening the Biological and Toxin Weapons Convention (BTWC) (Report). University of Bradford.
^ Pearson A (2006). "Incapacitating Biochemical Weapons". The Nonproliferation Review. 13 (2): 151–188. doi:10.1080/10736700601012029.
^ Schmidt U (August 2019). "Creating a 'Father Confessor': the origins of research ethics committees in UK military medical research, 1950-1970. Part I, context and causes". Journal of the Royal Army Medical Corps. 165 (4): 284–290. doi:10.1136/jramc-2019-001206. PMID 31164389.

[1] Bentley KW, Hardy DG (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. Bibcode:1967JAChS..89.3281B. doi:10.1021/ja00989a032. PMID 6042764.

[2] Callaway S, Hollyhock WM, Ladell WS (1963). An Oripavine Derivative (TL2636) as a Potential Incapacitating Agent. Porton Technical Paper (Report). 835, PRO/WO189/357.

[3] Dando M (January 2006). The UK's Search for an Incapacitating ('Non-Lethal') Chemical Agent in the 1960s. Bradford Project on Strengthening the Biological and Toxin Weapons Convention (BTWC) (Report). University of Bradford.

[4] Pearson A (2006). "Incapacitating Biochemical Weapons". The Nonproliferation Review. 13 (2): 151–188. doi:10.1080/10736700601012029.

[pmid31164389-5] Schmidt U (August 2019). "Creating a 'Father Confessor': the origins of research ethics committees in UK military medical research, 1950-1970. Part I, context and causes". Journal of the Royal Army Medical Corps. 165 (4): 284–290. doi:10.1136/jramc-2019-001206. PMID 31164389.

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[2]

[3]

[4]

[5]

See also

References