AL-37350A: Difference between revisions

AL-37350A
Identifiers
	IUPAC name (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole;
CAS Number	362603-40-5 ;
PubChem CID	10331436;
IUPHAR/BPS	160;
ChemSpider	8506896 ;
UNII	KT54N4CC67;
ChEMBL	ChEMBL133455 ;
CompTox Dashboard (EPA)	DTXSID501350247 DTXSID10438239, DTXSID501350247 ;
Chemical and physical data
Formula	C14H18N2O
Molar mass	230.311 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O2c1ccc3c(c1CCC2)c(c[nH]3)C[C@@H](N)C;
	InChI InChI=1S/C14H18N2O/c1-9(15)7-10-8-16-12-4-5-13-11(14(10)12)3-2-6-17-13/h4-5,8-9,16H,2-3,6-7,15H2,1H3/t9-/m0/s1 ; Key:VVHJUSGIUWQPIT-VIFPVBQESA-N ;
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Latest revision as of 00:49, 1 November 2023

AL-37350A (4,5-DHP-AMT) is a tricyclic tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT_2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT_2B and 5-HT_2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma.^[1]

References

^ May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA (September 2003). "A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole". Journal of Medicinal Chemistry. 46 (19): 4188–95. CiteSeerX 10.1.1.688.6169. doi:10.1021/jm030205t. PMID 12954071.

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[pmid12954071-1] May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA (September 2003). "A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole". Journal of Medicinal Chemistry. 46 (19): 4188–95. CiteSeerX 10.1.1.688.6169. doi:10.1021/jm030205t. PMID 12954071.

[1]

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{Drugbox
+| Verifiedfields = changed
+| Watchedfields = changed
 | verifiedrevid = 477346561
 | IUPAC_name = (''S'')-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-''e'']indole
-| image = AL-37350A_structure.png
+| image = AL-37350A Structure.svg
 | width = 140
@@ Line 15: / Line 18: @@
 | legal_US =
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
@@ Line 22: / Line 25: @@
 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
-| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number_Ref = {{cascite|correct|CAS}}
 | CAS_number = 362603-40-5
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = KT54N4CC67
 | ATC_prefix =
 | ATC_suffix =
@@ Line 33: / Line 38: @@
 | PubChem = 10331436
 | IUPHAR_ligand = 160
-|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 8506896
-|  SMILES = O2c1ccc3c(c1CCC2)c(cn3)C[C@@H](N)C
-|  InChI = 1/C14H18N2O/c1-9(15)7-10-8-16-12-4-5-13-11(14(10)12)3-2-6-17-13/h4-5,8-9,16H,2-3,6-7,15H2,1H3/t9-/m0/s1
-|  InChIKey = VVHJUSGIUWQPIT-VIFPVBQEBB
-|  StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| StdInChI = 1S/C14H18N2O/c1-9(15)7-10-8-16-12-4-5-13-11(14(10)12)3-2-6-17-13/h4-5,8-9,16H,2-3,6-7,15H2,1H3/t9-/m0/s1
-|  StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| StdInChIKey = VVHJUSGIUWQPIT-VIFPVBQESA-N
 <!--Chemical data-->
 | C=14 | H=18 | N=2 | O=1
+| smiles = O2c1ccc3c(c1CCC2)c(c[nH]3)C[C@@H](N)C
-| molecular_weight = 230.305 g/mol
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| smiles = CC(N)Cc3cnc2ccc1OCCCc1c23
+| StdInChI = 1S/C14H18N2O/c1-9(15)7-10-8-16-12-4-5-13-11(14(10)12)3-2-6-17-13/h4-5,8-9,16H,2-3,6-7,15H2,1H3/t9-/m0/s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = VVHJUSGIUWQPIT-VIFPVBQESA-N
 | melting_point =
 | melting_high =
 }}
+'''AL-37350A''' ('''4,5-DHP-AMT''') is a tricyclic [[tryptamine]] derivative which acts as a potent and selective [[agonist]] for the [[serotonin]] [[Receptor (biochemistry)|receptor]] [[5-HT2A receptor|5-HT<sub>2A</sub>]], with a [[Dissociation constant#Protein-ligand binding|Ki]] of 2.0 nM, and moderate selectivity over the related 5-HT<sub>2B</sub> and 5-HT<sub>2C</sub> receptors. It has been shown to have [[Intraocular pressure|ocular hypotensive]] activity in animal models, suggesting it may be useful for the treatment of [[glaucoma]].<ref name="pmid12954071">{{cite journal |vauthors =May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA |title=A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole |journal=Journal of Medicinal Chemistry |volume=46 |issue=19 |pages=4188–95 |date=September 2003 |pmid=12954071 |doi=10.1021/jm030205t |citeseerx=10.1.1.688.6169 }}</ref>
-'''AL-37350A''' ('''4,5-DHP-AMT''') is a [[tryptamine]] derivative which acts as a potent and selective [[agonist]] for the [[serotonin]] [[Receptor (biochemistry)|receptor]] [[5-HT2A receptor|5-HT<sub>2A</sub>]], with a [[Dissociation constant#Protein-ligand binding|Ki]] of 2.0 nM, and moderate selectivity over the related 5-HT<sub>2B</sub> and 5-HT<sub>2C</sub> receptors. It has been shown to have [[Intraocular pressure|ocular hypotensive]] activity in animal models, suggesting it may be useful for the treament of [[glaucoma]].<ref name="pmid12954071">{{cite journal |author=May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA |title=A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole |journal=Journal of Medicinal Chemistry |volume=46 |issue=19 |pages=4188–95 |year=2003 |month=September |pmid=12954071 |doi=10.1021/jm030205t |url=}}</ref>
 ==See also==
+* [[Ramelteon]]
 * [[AL-38022A]]
+* [[CP-132,484]]
 * [[1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole|4,5-DHP-DMT]]
@@ Line 60: / Line 62: @@
 {{reflist}}
+{{Hallucinogens}}
 {{Serotonergics}}
 {{Tryptamines}}
+[[Category:Dihydropyrans]]
 [[Category:Serotonin receptor agonists]]
 [[Category:Tryptamines]]
-[[Category:Pyrans]]

v t e Tryptamines
Tryptamines	1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-EPT 4-AcO-NMT 4-AcO-MALT 4-AcO-MET 4-AcO-DPT 4-AcO-MiPT 4-F-5-MeO-DMT 4-HO-5-MeO-DMT 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DiPT 4-HO-DPT 4-HO-DSBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-CT 5-Chloro-DMT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-HO-DiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T-NBOMe 5-MeS-DMT 5-Methoxytryptamine (5-MT; mexamine) 5-Methyl-DMT 5-Methyltryptamine 5-MT-NB3OMe 5-(Nonyloxy)tryptamine 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 7-Methyl-DMT Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Lespedamine MET Methylbutyltryptamine Miprocin (4-HO-MiPT) MiPT MPT Milipertine MS-245 MSBT N-Feruloylserotonin (moschamine) NET NMT Norbaeocystin (4-PO-T) NTBT O-4310 Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BNC-210 BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Flucindole Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH, 9-Me-BC, β-carboline (norharman), harmaline, harmalol, harmane, harmine, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids and related (e.g., DM-506 (ibogaminalog), ibogaine, ibogamine, noribogaine, tabernanthalog, tabernanthine) Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAL 5-MIAL 7-Aza-5-MeO-DiPT AAZ-A-154 AL-34662 AL-38022A BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Pirlindole (R)-69 (3IQ) Ro60-0175 Ro60-0213 RU-24,969 Sertindole SN-22 Substituted benzofurans (e.g., 3-APB, 5-MeO-DiBF, BPAP, dimemebfe, mebfap) Tepirindole Tetrindole Triptans (e.g., avitriptan, LY-334370, naratriptan) VER-3323 VU6067416 YM-348