THC morpholinylbutyrate

THC morpholinylbutyrate
Identifiers
	IUPAC name [(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] 4-morpholin-4-ylbutanoate;
CAS Number	55602-38-5 [EPA];
PubChem CID	6453212;
ChemSpider	4955601;
UNII	77FJY4KZ74;
ChEMBL	ChEMBL3301967;
CompTox Dashboard (EPA)	DTXSID30204150 ;
Chemical and physical data
Formula	C29H43NO4
Molar mass	469.666 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCCN4CCOCC4;
	InChI InChI=1S/C29H43NO4/c1-5-6-7-9-22-19-25(33-27(31)10-8-13-30-14-16-32-17-15-30)28-23-18-21(2)11-12-24(23)29(3,4)34-26(28)20-22/h18-20,23-24H,5-17H2,1-4H3/t23-,24-/m1/s1; Key:HAQNKTBQOIAWDB-DNQXCXABSA-N;

THC morpholinylbutyrate (SP-111, Δ⁹-THC-O-[4-(morpholin-4-yl)butyrate]) is a synthetic derivative of tetrahydrocannabinol, developed in the 1970s. It is a prodrug which is converted into THC inside the body, and was one of the first derivatives of THC that is able to form water-soluble salts, giving it a significant advantage over THC for some applications. However, it is less potent than THC and the metabolic conversion to THC is relatively slow and variable, giving it unpredictable pharmacokinetics which has limited its research applications.^[1]^[2]^[3]^[4]

References

^ Dykstra LA, McMillan DE, Harris LS (1975). "Effects of delta-9-THC and a water soluble ester of delta-9-THC on schedule-controlled behavior". Pharmacology, Biochemistry, and Behavior. 3 (1): 29–32. doi:10.1016/0091-3057(75)90077-5. PMID 1129353. S2CID 140206443.
^ Segal M (January 1978). "The effects of SP-111, a water-soluble THC derivative, on neuronal activity in the rat brain". Brain Research. 139 (2): 263–75. doi:10.1016/0006-8993(78)90928-9. PMID 624059. S2CID 35922918.
^ Hershkowitz M, Szechtman H (November 1979). "Pretreatment with delta 1-tetrahydrocannabinol and psychoactive drugs: effects on uptake of biogenic amines and on behavior". European Journal of Pharmacology. 59 (3–4): 267–76. doi:10.1016/0014-2999(79)90290-5. PMID 230975.
^ Järbe TU, McMillan DE (1980). "delta 9-THC as a discriminative stimulus in rats and pigeons: generalization to THC metabolites and SP-111". Psychopharmacology. 71 (3): 281–9. doi:10.1007/BF00433063. PMID 6256796. S2CID 11048922.

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[1] Dykstra LA, McMillan DE, Harris LS (1975). "Effects of delta-9-THC and a water soluble ester of delta-9-THC on schedule-controlled behavior". Pharmacology, Biochemistry, and Behavior. 3 (1): 29–32. doi:10.1016/0091-3057(75)90077-5. PMID 1129353. S2CID 140206443.

[2] Segal M (January 1978). "The effects of SP-111, a water-soluble THC derivative, on neuronal activity in the rat brain". Brain Research. 139 (2): 263–75. doi:10.1016/0006-8993(78)90928-9. PMID 624059. S2CID 35922918.

[3] Hershkowitz M, Szechtman H (November 1979). "Pretreatment with delta 1-tetrahydrocannabinol and psychoactive drugs: effects on uptake of biogenic amines and on behavior". European Journal of Pharmacology. 59 (3–4): 267–76. doi:10.1016/0014-2999(79)90290-5. PMID 230975.

[4] Järbe TU, McMillan DE (1980). "delta 9-THC as a discriminative stimulus in rats and pigeons: generalization to THC metabolites and SP-111". Psychopharmacology. 71 (3): 281–9. doi:10.1007/BF00433063. PMID 6256796. S2CID 11048922.

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[2]

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[4]

Identifiers

IUPAC name [(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] 4-morpholin-4-ylbutanoate
CAS Number	55602-38-5^Y[EPA]
PubChem CID	6453212
ChemSpider	4955601
UNII	77FJY4KZ74
ChEMBL	ChEMBL3301967
CompTox Dashboard (EPA)	DTXSID30204150
Chemical and physical data
Formula	C₂₉H₄₃NO₄
Molar mass	469.666 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCCN4CCOCC4
InChI InChI=1S/C29H43NO4/c1-5-6-7-9-22-19-25(33-27(31)10-8-13-30-14-16-32-17-15-30)28-23-18-21(2)11-12-24(23)29(3,4)34-26(28)20-22/h18-20,23-24H,5-17H2,1-4H3/t23-,24-/m1/s1 Key:HAQNKTBQOIAWDB-DNQXCXABSA-N

THC morpholinylbutyrate

See also

References