FGIN-127

FGIN-127
Identifiers
	IUPAC name 2-[2-(4-fluorophenyl)-1H-indol-3-yl]-N,N-dihexylacetamide;
CAS Number	142720-24-9 ;
PubChem CID	132496;
ChemSpider	116994 ;
ChEBI	CHEBI:92171 ;
Chemical and physical data
Formula	C28H37FN2O
Molar mass	436.615 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCN(CCCCCC)C(=O)Cc1c2ccccc2[nH]c1c3ccc(cc3)F;
	InChI InChI=1S/C28H37FN2O/c1-3-5-7-11-19-31(20-12-8-6-4-2)27(32)21-25-24-13-9-10-14-26(24)30-28(25)22-15-17-23(29)18-16-22/h9-10,13-18,30H,3-8,11-12,19-21H2,1-2H3 ; Key:VUWXAQFLTSBUDB-UHFFFAOYSA-N ;
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Short description: Chemical compound

FGIN-1-27 is an anxiolytic drug which acts as a selective agonist at the peripheral benzodiazepine receptor, also known as the mitochondrial 18 kDa translocator protein or TSPO. It is thought to produce anxiolytic effects by stimulating steroidogenesis of neuroactive steroids such as allopregnanolone.^[1]^[2]^[3]^[4]^[5]^[6]

References

↑ "2-Aryl-3-indoleacetamides (FGIN-1): a new class of potent and specific ligands for the mitochondrial DBI receptor (MDR)". The Journal of Pharmacology and Experimental Therapeutics 262 (3): 971–8. September 1992. PMID 1326631.
↑ "Stimulation of brain steroidogenesis by 2-aryl-indole-3-acetamide derivatives acting at the mitochondrial diazepam-binding inhibitor receptor complex". The Journal of Pharmacology and Experimental Therapeutics 267 (1): 462–71. October 1993. PMID 8229777.
↑ "Synthesis and preliminary behavioural evaluation in mice of new 3-aryl-3-pyrrol-1-ylpropanamides, analogues of FGIN-1-27 and FGIN-1-43". The Journal of Pharmacy and Pharmacology 53 (11): 1561–8. November 2001. doi:10.1211/0022357011777945. PMID 11732760.
↑ "In the ventral tegmental area picrotoxin blocks FGIN 1-27-induced increases in sexual behavior of rats and hamsters". Psychopharmacology 178 (2–3): 174–82. March 2005. doi:10.1007/s00213-004-2001-9. PMID 15338106.
↑ "Preparation of indoles from alpha-aminonitriles: A short synthesis of FGIN-1-27". Organic Letters 8 (20): 4473–5. September 2006. doi:10.1021/ol061617+. PMID 16986928.
↑ "Development of ligands for the peripheral benzodiazepine receptor". Current Medicinal Chemistry 13 (17): 1991–2001. 2006. doi:10.2174/092986706777584979. PMID 16842193. https://flore.unifi.it/bitstream/2158/222808/1/id%20222808.pdf.

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[pmid1326631-1] "2-Aryl-3-indoleacetamides (FGIN-1): a new class of potent and specific ligands for the mitochondrial DBI receptor (MDR)". The Journal of Pharmacology and Experimental Therapeutics 262 (3): 971–8. September 1992. PMID 1326631.

[pmid8229777-2] "Stimulation of brain steroidogenesis by 2-aryl-indole-3-acetamide derivatives acting at the mitochondrial diazepam-binding inhibitor receptor complex". The Journal of Pharmacology and Experimental Therapeutics 267 (1): 462–71. October 1993. PMID 8229777.

[pmid11732760-3] "Synthesis and preliminary behavioural evaluation in mice of new 3-aryl-3-pyrrol-1-ylpropanamides, analogues of FGIN-1-27 and FGIN-1-43". The Journal of Pharmacy and Pharmacology 53 (11): 1561–8. November 2001. doi:10.1211/0022357011777945. PMID 11732760.

[pmid15338106-4] "In the ventral tegmental area picrotoxin blocks FGIN 1-27-induced increases in sexual behavior of rats and hamsters". Psychopharmacology 178 (2–3): 174–82. March 2005. doi:10.1007/s00213-004-2001-9. PMID 15338106.

[pmid16986928-5] "Preparation of indoles from alpha-aminonitriles: A short synthesis of FGIN-1-27". Organic Letters 8 (20): 4473–5. September 2006. doi:10.1021/ol061617+. PMID 16986928.

[pmid16842193-6] "Development of ligands for the peripheral benzodiazepine receptor". Current Medicinal Chemistry 13 (17): 1991–2001. 2006. doi:10.2174/092986706777584979. PMID 16842193. https://flore.unifi.it/bitstream/2158/222808/1/id%20222808.pdf.

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v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Identifiers

IUPAC name 2-[2-(4-fluorophenyl)-1H-indol-3-yl]-N,N-dihexylacetamide
CAS Number	142720-24-9^Y
PubChem CID	132496
ChemSpider	116994^N
ChEBI	CHEBI:92171^N
Chemical and physical data
Formula	C₂₈H₃₇FN₂O
Molar mass	436.615 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCN(CCCCCC)C(=O)Cc1c2ccccc2[nH]c1c3ccc(cc3)F
InChI InChI=1S/C28H37FN2O/c1-3-5-7-11-19-31(20-12-8-6-4-2)27(32)21-25-24-13-9-10-14-26(24)30-28(25)22-15-17-23(29)18-16-22/h9-10,13-18,30H,3-8,11-12,19-21H2,1-2H3^N Key:VUWXAQFLTSBUDB-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

FGIN-127

Topic: Chemistry

References