Lysergic acid methyl ester

Lysergic acid methyl ester
Names

IUPAC name 7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9- carboxylic acid methyl ester
Other names Methyl lysergate
Identifiers
CAS Registry Number	4579-64-0
ChemSpider	9589747^Y
InChI InChI=1S/C17H18N2O2/c1-19-9-11(17(20)21-2)6-13-12-4-3-5-14-16(12)10(8-18-14)7-15(13)19/h3-6,8,11,15,18H,7,9H2,1-2H3/t11-,15-/m1/s1^Y Key: RNHDWLRHUJZABX-IAQYHMDHSA-N^Y InChI=1/C17H18N2O2/c1-19-9-11(17(20)21-2)6-13-12-4-3-5-14-16(12)10(8-18-14)7-15(13)19/h3-6,8,11,15,18H,7,9H2,1-2H3/t11-,15-/m1/s1 Key: RNHDWLRHUJZABX-IAQYHMDHBA
Jmol-3D images	Image
PubChem	11414860
SMILES O=C(OC)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
Properties
Molecular formula	C₁₇H₁₈N₂O₂
Molar mass	282.34 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Lysergic acid methyl ester is an analogue of lysergic acid diethylamide (LSD). It is a member of the tryptamine family and is extremely uncommon. It acts on the 5-HT receptors in the brain, as do most tryptamines.

References

External links

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 2-Butyllysergamide LSZ 3-Pentyllysergamide Methylergometrine Methylisopropyllysergamide Methysergide MLD-41 PARGY-LAD PRO-LAD

Phenethylamines	Aleph 2-Methyl-MDA 2C-B 2C-B-AN 2C-B-Dragonfly 2C-B-FLY 2CB-Ind βk-2C-B 2C-C 2C-C-FLY 2C-CP 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 25E-NBOMe 2C-EF 2C-F 25F-NBOMe 2C-G 25G-NBOMe 25H-NBOMe 2C-I βk-2C-I 2C-iP 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-3 2C-T-4 25T4-NBOMe 2C-T-7 2C-T-7-FLY 25T7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-21.5 2C-T-22 2C-T-27 2C-T-28 2C-TFE 2C-TFM 25TFM-NBOMe 2C-V 2C-YN 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25B-NBOH 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBF 25I-NBOMe 25P-NBOMe 3C-AL 3C-DFE 3C-E 3C-P 3C-TFE 4C-B 4C-D 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY Difluoroescaline Difluoromescaline DESOXY DMBMPP DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM DOYN BOB BOD BMB Escaline Fluoroproscaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Lophophine Macromerine MDA MDEA MDMA Mescaline Mescaline-NBOMe Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA Proscaline TCB-2 TFMFly Trifluoroescaline Trifluoromescaline TMA

Piperazines	pFPP TMFPP mCPP

Tryptamines	1-Me-5-MeO-DiPT 2,N,N-TMT 4,5-DHP-α-MT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DMT 4-AcO-DPT 4-AcO-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Ibogaine Iprocin MET Miprocin MiPT Norbaeocystin Noribogaine PiPT Psilocin Psilocybin Voacangine

Others	AL-38022A ALPHA Dimemebfe M-ALPHA RH-34

Dissociatives
NMDAR antagonists

Adamantanes	Amantadine Memantine Rimantadine

Arylcyclohexylamines	3-MeO-PCP 4-MeO-PCP Dieticyclidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others	2-MDP 8A-PDHQ Aptiganel Dexoxadrol Diphenidine Dizocilpine Etoxadrol Ibogaine Methoxphenidine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	4-HTMPIPO 5F-PB-22 AB-001 AB-005 A-836,339 AB-CHMINACA AB-FUBINACA AB-PINACA ADB-FUBINACA ADB-PINACA ADBICA AM-630 AM-679 AM-694 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-2201 AM-2232 AM-2233 APICA APINACA CB-13 CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 HU-308 JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-167 JWH-182 JWH-193 JWH-198 JWH-200 JWH-203 JWH-210 JWH-250 JWH-251 JWH-398 JWH-424 JTE 7-31 JTE-907 Levonantradol MAM-2201 MDA-19 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan Org 28611 Parahexyl QUCHIC QUPIC RCS-4 RCS-8 SDB-006 STS-135 THC-O-acetate THC-O-phosphate UR-144 WIN 55,212-2 XLR-11

D₂R agonists

Apomorphine
Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Piribedil
Pramipexole
Ropinirole
Rotigotine
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists

Inhalants
Mixed MOA

Aliphatic hydrocarbons
- Butane
- Gasoline
- Kerosene
- Propane
Aromatic hydrocarbons
- Toluene
Ethers
- Diethyl ether
- Enflurane
Haloalkanes
- Chlorofluorocarbons
- Chloroform

κOR agonists

MAO inhibitors

σR agonists

Others