THC morpholinylbutyrate

THC morpholinylbutyrate
Identifiers
  • [(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] 4-morpholin-4-ylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H43NO4
Molar mass469.666 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCCN4CCOCC4
  • 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]

  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.