VSN16R

VSN16R
Clinical data
Other names	SPG601; SPG-601
Identifiers
	IUPAC name 3-[(Z)-6-(dimethylamino)-6-oxohex-1-enyl]-N-[(2R)-1-hydroxypropan-2-yl]benzamide;
CAS Number	1246960-09-7;
PubChem CID	23730084;
ChemSpider	58827987;
UNII	D2QY1KLG2R;
ChEMBL	ChEMBL6068565;
Chemical and physical data
Formula	C18H26N2O3
Molar mass	318.417 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H](CO)NC(=O)C1=CC=CC(=C1)/C=C\CCCC(=O)N(C)C;
	InChI InChI=1S/C18H26N2O3/c1-14(13-21)19-18(23)16-10-7-9-15(12-16)8-5-4-6-11-17(22)20(2)3/h5,7-10,12,14,21H,4,6,11,13H2,1-3H3,(H,19,23)/b8-5-/t14-/m1/s1; Key:SVYRYFAUQHVGAI-BMWLXYDHSA-N;

VSN16R (SPG601) is a drug which acts as an opener of BK_Ca large-conductance, calcium-activated potassium channels. It is similar in chemical structure to some cannabinoid derivatives such as methanandamide and CB-86, and was originally thought to be an atypical cannabinoid compound, but pharmacological studies showed it to be inactive at both cannabinoid receptors and related receptors such as GPR55, and eventually it was found to be a selective BK_Ca channel opener. It has neuroprotective effects and reduces muscle spasticity, and is being researched as a potential therapeutic agent for the treatment of Fragile X syndrome.^[1]^[2]^[3]^[4]^[5]

References

^ Hoi PM, Visintin C, Okuyama M, Gardiner SM, Kaup SS, Bennett T, et al. (November 2007). "Vascular pharmacology of a novel cannabinoid-like compound, 3-(5-dimethylcarbamoyl-pent-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide (VSN16) in the rat". British Journal of Pharmacology. 152 (5): 751–764. doi:10.1038/sj.bjp.0707470. PMC 2190032. PMID 17891160.
^ Baker D, Pryce G, Visintin C, Sisay S, Bondarenko AI, Vanessa Ho WS, et al. (August 2017). "Big conductance calcium-activated potassium channel openers control spasticity without sedation". British Journal of Pharmacology. 174 (16): 2662–2681. doi:10.1111/bph.13889. PMC 5522996. PMID 28677901.
^ Tabatabaee S, Baker D, Selwood DL, Whalley BJ, Stephens GJ (July 2019). "The Cannabinoid-Like Compound, VSN16R, Acts on Large Conductance, Ca²⁺-Activated K⁺ Channels to Modulate Hippocampal CA1 Pyramidal Neuron Firing". Pharmaceuticals. 12 (3). Basel, Switzerland: 104. doi:10.3390/ph12030104. PMC 6789497. PMID 31277369.
^ Pryce G, Sisay S, Giovannoni G, Selwood DL, Baker D (July 2023). "Neuroprotection in an Experimental Model of Multiple Sclerosis via Opening of Big Conductance, Calcium-Activated Potassium Channels". Pharmaceuticals. 16 (7). Basel, Switzerland: 972. doi:10.3390/ph16070972. PMC 10383993. PMID 37513884.
^ Pedapati EV, Vanderklish PW, Sarraf ST, Gargosky S, Nelson M, Richter S, et al. (April 2026). "SPG601-associated modulation of resting-state EEG and improvement in executive function in a fragile X syndrome randomized controlled crossover study". Scientific Reports. 16 (1) 11705. Bibcode:2026NatSR..1611705P. doi:10.1038/s41598-026-46928-6. PMC 13062090. PMID 41946887.

[1] Hoi PM, Visintin C, Okuyama M, Gardiner SM, Kaup SS, Bennett T, et al. (November 2007). "Vascular pharmacology of a novel cannabinoid-like compound, 3-(5-dimethylcarbamoyl-pent-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide (VSN16) in the rat". British Journal of Pharmacology. 152 (5): 751–764. doi:10.1038/sj.bjp.0707470. PMC 2190032. PMID 17891160.

[2] Baker D, Pryce G, Visintin C, Sisay S, Bondarenko AI, Vanessa Ho WS, et al. (August 2017). "Big conductance calcium-activated potassium channel openers control spasticity without sedation". British Journal of Pharmacology. 174 (16): 2662–2681. doi:10.1111/bph.13889. PMC 5522996. PMID 28677901.

[3] Tabatabaee S, Baker D, Selwood DL, Whalley BJ, Stephens GJ (July 2019). "The Cannabinoid-Like Compound, VSN16R, Acts on Large Conductance, Ca²⁺-Activated K⁺ Channels to Modulate Hippocampal CA1 Pyramidal Neuron Firing". Pharmaceuticals. 12 (3). Basel, Switzerland: 104. doi:10.3390/ph12030104. PMC 6789497. PMID 31277369.

[4] Pryce G, Sisay S, Giovannoni G, Selwood DL, Baker D (July 2023). "Neuroprotection in an Experimental Model of Multiple Sclerosis via Opening of Big Conductance, Calcium-Activated Potassium Channels". Pharmaceuticals. 16 (7). Basel, Switzerland: 972. doi:10.3390/ph16070972. PMC 10383993. PMID 37513884.

[5] Pedapati EV, Vanderklish PW, Sarraf ST, Gargosky S, Nelson M, Richter S, et al. (April 2026). "SPG601-associated modulation of resting-state EEG and improvement in executive function in a fragile X syndrome randomized controlled crossover study". Scientific Reports. 16 (1) 11705. Bibcode:2026NatSR..1611705P. doi:10.1038/s41598-026-46928-6. PMC 13062090. PMID 41946887.

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See also

References