THC-VHS

THC-VHS
Identifiers
	IUPAC name 4-{[3-Methyl-1-oxo-1-(6,6,9-trimethyl-3-pentylbenzo[c]chromen-1-yl)oxybutan-2-yl]amino}-4-oxobutanoic acid;
PubChem CID	155242207;
Chemical and physical data
Formula	C30H39NO6
Molar mass	509.643 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C)Oc2cc(cc(OC(=O)[C@H](NC(=O)CCC(=O)O)C(C)C)c2[C@@H]2C=C(C)CC[C@H]21)CCCCC;
	InChI InChI=1S/C30H43NO6/c1-7-8-9-10-20-16-23(36-29(35)28(18(2)3)31-25(32)13-14-26(33)34)27-21-15-19(4)11-12-22(21)30(5,6)37-24(27)17-20/h15-18,21-22,28H,7-14H2,1-6H3,(H,31,32)(H,33,34)/t21-,22-,28-/m1/s1; Key:QAIKRQKSCBZKKS-DQCZWYHMSA-N;

THC valine hemisuccinate (THC-VHS, NB-1111, SBI-100) is a synthetic prodrug of tetrahydrocannabinol, developed at the University of Mississippi as a stabilised formulation for ophthalmic administration, for use in the treatment of glaucoma and other eye conditions requiring reduction in intraocular pressure.^[1]^[2]^[3]^[4]^[5]

References

^ Taskar PS, Patil A, Lakhani P, Ashour E, Gul W, ElSohly MA, et al. (September 2019). "Δ9-Tetrahydrocannabinol Derivative-Loaded Nanoformulation Lowers Intraocular Pressure in Normotensive Rabbits". Translational Vision Science & Technology. 8 (5): 15. doi:10.1167/tvst.8.5.15. PMC 6753841. PMID 31588378.
^ Sweeney C, Dudhipala N, Thakkar R, Mehraj T, Marathe S, Gul W, et al. (October 2021). "Effect of surfactant concentration and sterilization process on intraocular pressure-lowering activity of Δ9-tetrahydrocannabinol-valine-hemisuccinate (NB1111) nanoemulsions". Drug Delivery and Translational Research. 11 (5): 2096–2107. doi:10.1007/s13346-020-00871-9. PMID 33169348.
^ Sweeney C, Dudhipala N, Thakkar R, Mehraj T, Marathe S, Gul W, et al. (March 2022). "Impact of mucoadhesive agent inclusion on the intraocular pressure lowering profile of Δ9-tetrahydrocannabinol-valine-hemisuccinate loaded nanoemulsions in New Zealand white rabbits". International Journal of Pharmaceutics. 616: 121564. doi:10.1016/j.ijpharm.2022.121564. PMID 35151817.
^ US 8809261, Elsohly MA, Gul W, Repka MA, Majumdar S, "Compositions containing delta-9-THC-amino acid esters and process of preparation.", issued 19 August 2014, assigned to ElSohly Laboratories, Inc.
^ WO 2020/215164, Hsu E, Kumar U, Kumar R, "Compositions and methods for use of cannabinoids for neuroprotection", published 29 October 2020, assigned to Inmed Pharmaceuticals Inc.

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Identifiers

IUPAC name 4-{[3-Methyl-1-oxo-1-(6,6,9-trimethyl-3-pentylbenzo[c]chromen-1-yl)oxybutan-2-yl]amino}-4-oxobutanoic acid
PubChem CID	155242207
Chemical and physical data
Formula	C₃₀H₃₉NO₆
Molar mass	509.643 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1(C)Oc2cc(cc(OC(=O)[C@H](NC(=O)CCC(=O)O)C(C)C)c2[C@@H]2C=C(C)CC[C@H]21)CCCCC
InChI InChI=1S/C30H43NO6/c1-7-8-9-10-20-16-23(36-29(35)28(18(2)3)31-25(32)13-14-26(33)34)27-21-15-19(4)11-12-22(21)30(5,6)37-24(27)17-20/h15-18,21-22,28H,7-14H2,1-6H3,(H,31,32)(H,33,34)/t21-,22-,28-/m1/s1 Key:QAIKRQKSCBZKKS-DQCZWYHMSA-N