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CYP-LAD
Clinical data

Other names	N,N-Diethyl-6-cyclopropyl-6-norlysergamide; 6-Cyclopropyl-6-norlysergic acid diethylamide; 6-Cyclopropyl-6-nor-LSD; TRALA-22; 6-Cyclopropyl-N,N-diethyl-9,10-didehydroergoline-8β-carboxamide
Identifiers
IUPAC name (6aR,9R)-7-cyclopropyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number	3024530-20-6
PubChem CID	60210039
ChemSpider	21106273^Y
Chemical and physical data
Formula	C₂₂H₂₇N₃O
Molar mass	349.478 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C5CC5
InChI InChI=1S/C22H27N3O/c1-3-24(4-2)22(26)15-10-18-17-6-5-7-19-21(17)14(12-23-19)11-20(18)25(13-15)16-8-9-16/h5-7,10,12,15-16,20,23H,3-4,8-9,11,13H2,1-2H3/t15-,20-/m1/s1 Key:LICTYPNIKGFVGH-FOIQADDNSA-N
(verify)

CYP-LAD, also known as 6-cyclopropyl-6-nor-lysergic acid diethylamide or as TRALA-22, is a lysergamide and analogue of lysergic acid diethylamide (LSD).^[1] It was patented by Daniel Trachsel and colleagues in 2023 as an LSD analogue with modified LSD-like action,^[1] and had also previously been claimed in a 2022 patent by Gilgamesh Pharmaceuticals.^[2]

References

^ ^a ^b US 2023/0414583, Trachsel D, Liechti ME, Lustenberger F, "Lysergic acid derivatives with modified LSD-like action", published 28 December 2023, assigned to Mind Medicine Inc.
^ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408

External links

CYP-LAD - Isomer Design

No ring subs.	CYB004 (deuDMT) DALT DBT DCPT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT 4-HO-MALT 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acetoxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MET (metocetin) 4-AcO-MiPT (mipracetin) 4-GO-DiPT (RE-104, FT-104) 4-GO-DMT (RE-109) 4-PrO-DMT
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-(t-BuCO)-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 4,N,N-TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N,N-TMT 7,N,N-TMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) 5-Methoxy-α-alkyltryptamines: 5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g., LSD) β-Carbolines and Harmala alkaloids (e.g., harmine, harmaline, 6-methoxyharmalan) Iboga alkaloids (e.g., 18-MAC, 18-MC, coronaridine, ibogaine, ibogamine, ME-18-MC, noribogaine, tabernanthine, voacangine) Ibogalogs (e.g., ibogainalog) O-Methylnordehydrobufotenine Partial ergolines (e.g., NDTDI, RU-28306, CT-5252) Piperidinylethylindoles (e.g., Pip-T) Pyrrolidinylethylindoles (e.g., Pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI)
Bioisosteres	Benzofurans (e.g., 5-MeO-DiBF, dimemebfe (5-MeO-BFE), mebfap) Benzothiophenes (e.g., 3-APBT) Indazoles (e.g., AL-38022A, O-methyl-AL-34662) Indenes (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175) MYCO-005 Quinolinylethylamines (e.g., mefloquine)

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metaescaline Methallylescaline N-Methylmescaline (M-M) NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-SE 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x: 2C-O 2C-O-2 2C-O-4 Others: 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOH-2C-B) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CE-5iPrO, 2CT2-5-ETO, ASR-2001 (2CB-5PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA
DOx	DOB DOC DOEF DOET DOI DOiPR DOM DON DOPR DOTFM Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: DOM-NBOMe Ganeshas (G-x) (e.g., Ganesha (G, G-1)
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA IDA Lophophine (MMDPEA) Lys-MDA Lys-MDMA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe: 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others: 25B-NB (N-benzyl-2C-B) 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) CT-5172 DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) TMAs (e.g., TMA-3, TMA-4, TMA-5, TMA-6) TOMSO ZDCM-04 Structure undisclosed: CYB005
Cyclized	1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzazepines (e.g., lorcaserin) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Glaucine IHCH-7113 Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Z3517967757 ZC-B

1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

Other ring system-substituted lysergamides: 12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres: JRT

Others

Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP)
Dihydrobenzoxazines (e.g., efavirenz)
Phenoxyethylamines (e.g., CT-4719, ORG-37684)
Quinazolinylethylamines (e.g., RH-34)

Natural sources

Cyclized tryptamines: Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Trichocereus cacti (e.g., San Pedro, Peruvian torch)

v t e Ergolines
Ergolines (incl. lysergines)	13-Fluorolysergol Acetergamine Brazergoline Bromerguride (2-bromolisuride) Cianergoline Delergotrile Descarboxylysergic acid Dihydrolysergic acid Disulergine Dosergoside Ergolene Ergoline Etisulergine Lergotrile Lisuride Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mesulergine Metergoline Nicergoline Pergolide Pibocin B Proterguride Romergoline Sergolexole Terguride Tiomergine
Clavines (6,8-dimethylergolines)	6,8-Dimethylergoline (clavine) 9-Deacetoxyfumigaclavine C Agroclavine Costaclavin Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Penniclavine Setoclavine Partial ergolines and related: Chanoclavine Chanoclavine II Cycloclavine Paliclavine
Lysergamides (lysergic acid amides)	Non-hallucinogenic lysergamides: 1P-BOL-148 2-Bromo-LSD (bromolysergide; BOL-148) 2-Iodo-LSD 2-Oxo-LSD (2-keto-LSD) 9,10-Dihydro-LSD 12-Hydroxy-LSD 12-Methoxy-LSD Amesergide Cabergoline Ergometrinine Iso-LSD LY-215,840 Lysergic acid cyclobutylamide (LAcB) Lysergic acid cyclopentylamide (cepentil; LCyP) Lysergic acid dibutylamide (LBB-66) MBL-61 (2-bromo-1-methyl-LSD) MIL (1-methyl-2-iodo-LSD) SPT-348 Psychedelic lysergamides: 1B-LSD 1cP-AL-LAD 1cP-LSD 1D-LSD 1DD-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MIPLA 1S-LSD 1T-AL-LAD 1T-LSD 1V-LSD 2,3-Dihydro-LSD AL-LAD ALA-10 (1-acetyl-LAE) ALD-52 (1-acetyl-LSD) BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) Dipropyllysergamide (DPL) Ergine (lysergic acid amide; LSA; LA-111; lysergamide) Ergometrine (ergonovine, ergobasine) ETH-LAD Ethylcyclopropyllysergamide (ECPLA) Ethylisopropyllysergamide (EIPLA) Ethylpropyllysergamide (EPLA; LEP-57) Ethyltrifluoroethyllysergamide (ETFELA) IP-LAD Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide) Methylpropyllysergamide (LAMPA) Lysergic acid diethylamide (LSD; lysergide) Lysergic acid ethylamide (LAE-32, LAE) Lysergic acid hydroxyethylamide (LSH) Lysergic acid methylamide (LAM) Lysergic acid methylethylamide (LME-54) Lysergic acid morpholide (LSM-775) Lysergic acid propylamide (LAP) Lysergic acid pyrrolidide (LPD-824) Lysergic acid 2-butylamide (LSB) Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) Lysergic acid 3-pentylamide (LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MIPLA) Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyllysergic acid pyrrolidide) OML-632 (1-hydroxymethyl-LSD) PARGY-LAD PRO-LAD Unsorted lysergamides: 13-Fluoro-LSD 13-Hydroxy-LSD 14-Hydroxy-LSD CE-LAD Dihydroergometrine (dihydroergonovine, dihydroergobasine) FLUORETH-LAD Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) Lysergic acid ethyl-2-hydroxyethylamide (LEO) Lysergic acid isopropylamide (LAiP) Lysergic acid piperidide (LA-Pip, LSD-Pip) Lysergic acid pyrrolinide (LPN) Lysergic acid tert-butylamide (LAtB) Propisergide (1-methylergonovine)
Ergopeptines (peptide ergolines)	Bromocriptine Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergosine Dihydroergotamine Epicriptine Ergocornine Ergocristine Ergocryptine Ergoloid (dihydroergotoxine; Hydergine) Ergonine Ergosine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Mergocriptine Metergotamine
Partial ergolines	2-Aminotetralins (e.g., 8-OH-DPAT) 3,4-DMPEA-NDEPA 5-MeO-N-DEAOP-NET 5-MeO-N-DEAOP-NMT 10,11-Secoergoline (α,N-Pip-T) 10,11-Seco-LSD 25B-NAcPip 25D-NM-NDEAOP (25D-NM-NDEPA) Bay R 1531 (LY-197206) CT-5252 DEIMDHPCA (3,5-seco-LSD) DEMPDHPCA DEMPDHPCA-2C-D DEMPDHPCA-mescaline DEMPDHPCA-NAP DEMPDHPCA-PMA DOB-NDEPA DOI-NDEPA DOM-NDEPA DOTFM-NDEPA FAEFHI FHATHBIN LPH-5 LY-178210 LY-293284 M-NDEPA N-DEAOP-NMPEA (PEA-NM-NDEPA) N-DEAOP-NMT NDTDI (8,10-seco-LSD) Phenethylamines RU-27251 RU-27849 RU-28251 RU-28306 TMA-2-NDEPA Tryptamines WXVL_BT0793LQ2118 Related: Nikethamide Tochergamine
Related compounds	A-86929 Adrogolide CY-208,243 JRT Naxagolide Quinagolide SDZ SER-082 Voxergolide
Natural sources	Fungi: Clavicipitaceae Claviceps spp. (ergot) Claviceps paspali Claviceps purpurea Epichloë spp. Periglandula spp. Periglandula clandestina Periglandula ipomoeae Periglandula turbinae Plants (infected/symbiotic with the above fungi): Achnatherum robustum (sleepy grass) Convolvulaceae (morning glory) Argyreia nervosa (Hawaiian baby woodrose) Ipomoea asarifolia (ginger-leaf morning-glory) Ipomoea corymbosa (coaxihuitl, ololiúqui) Ipomoea tricolor (tlitliltzin, badoh negro)
See also: Tryptamines Phenethylamines Psychedelics

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