Lysergol supplier | CasNO.602-85-7

Name
LYSERGOL
EINECS 210-024-5
CAS No. 602-85-7
Article Data16
CAS DataBase
Density 1.3 g/cm³
Solubility
Melting Point 248°C
Formula C₁₆H₁₈N₂O
Boiling Point 465.8 °C at 760 mmHg
Molecular Weight 254.332
Flash Point 235.5 °C
Transport Information UN 1544
Appearance Off-white to beige crystalline powder
Safety 26-36/37/39-45
Risk Codes 26/27/28
Molecular Structure
Hazard Symbols T+
Synonyms 9,10-Didehydro-6-methyl-8-hydroxymethylergoline;Ergoline, 9,10-didehydro-8-hydroxymethyl-6-methyl-;9,10-Didehydro-6-methylergoline-8beta-methanol;Ergoline-8-methanol, 9,10-didehydro-6-methyl-, (8-beta)-(9CI);Ergoline-8beta-methanol, 9,10-didehydro-6-methyl- (8CI);BRN 0088476;NSC 196867;[(8β)-6-Methyl-9,10-didehydroergolin-8-yl]methanol;
PSA 39.26000
LogP 1.96780

Synthetic route

: ((6aR,9R)-7-methyl-4-tosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

: 602-85-7
lysergol

Conditions

Conditions	Yield
With magnesium In methanol Inert atmosphere;	93%

: 1159774-79-4
lysergic acid methyl ester

A: 478-93-3
((6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

B: 602-85-7
lysergol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.166667h;	A 24% B 49%

: 478-91-1
Lysergen

: 602-85-7
lysergol

Conditions

Conditions	Yield
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1.) THF, 60 deg C, 24 h, 2.) THF, 40 deg C, 2 h; Yield given. Multistep reaction;

6-methyl-9,10-didehydro-ergoline-8β-carboxylic acid methyl ester: 6-methyl-9,10-didehydro-ergoline-8β-carboxylic acid methyl ester

: 602-85-7
lysergol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

elymoclavine: elymoclavine

: 602-85-7
lysergol

Conditions

Conditions	Yield
With sodium butanolate; butan-1-ol

elymoclavine: elymoclavine

A: 602-85-7
lysergol

B isolysergol, lysergene: isolysergol, lysergene

Conditions

Conditions	Yield
With potassium hydroxide at 140℃;

: 548-43-6
elymoclavine

: 2372-45-4
sodium butanolate

: 71-36-3
butan-1-ol

A: 478-93-3
((6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

B: 602-85-7
lysergol

C lysergene: lysergene

...Expand

: 548-43-6
elymoclavine

methanol. KOH: methanol. KOH

A: 478-93-3
((6aR,9S)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

B: 602-85-7
lysergol

C lysergene: lysergene

Conditions

Conditions	Yield
at 140℃;

...Expand

: 519-12-0
(+)-setoclavine

: 602-85-7
lysergol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.34 g / Woelm alumina / toluene / 2.5 h / Heating 2: 1.) 9-BBN, 2.) NaOH, 30percent aq. H2O2 / 1.) THF, 60 deg C, 24 h, 2.) THF, 40 deg C, 2 h View Scheme

: ((6aR,9R)-4,7-ditosyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

: 602-85-7
lysergol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium naphthalenide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 2: sodium cyanoborohydride; acetic acid / methanol / 1 h / 25 °C / Inert atmosphere View Scheme

: 50-00-0
formaldehyd

: 80233-17-6
lysergol

: 602-85-7
lysergol

Conditions

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 25℃; for 1h; Inert atmosphere;	5.2 mg

: C25H26N2O4S

: 602-85-7
lysergol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 2: magnesium / methanol / Inert atmosphere View Scheme

: 602-85-7
lysergol

: 18051-16-6
9,10-dihydrolysergol

Conditions

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In N,N-dimethyl-formamide at 50 - 60℃; under 2068.65 - 2585.81 Torr;	97%
With methanol; nickel In 1,4-dioxane Heating;	90%
With methanol; Ra-Ni In 1,4-dioxane for 0.25h; Product distribution; Heating; different ratio of the solvents and times;
With hydrogen; palladium on activated charcoal In pyridine; N,N-dimethyl-formamide under 3750.3 Torr;

: 18162-48-6
tert-butyldimethylsilyl chloride

: 602-85-7
lysergol

: 1075250-72-4
8β-(tert-butyldimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 4 - 5h;	96.5%

: 108-24-7
acetic anhydride

: 602-85-7
lysergol

: 85892-92-8
(5R)-6-methyl-(8R)-acetoxymethyl-Δ9,10-ergolene

Conditions

Conditions	Yield
With pyridine Ambient temperature;	90%
In pyridine Ambient temperature;	90%
With pyridine
In pyridine Ambient temperature; Yield given;

: 67-56-1
methanol

: 602-85-7
lysergol

: 35121-60-9
10alpha-methoxy-9,10-dihydrolysergol

Conditions

Conditions	Yield
With sulfuric acid at 20 - 40℃; for 6h; Inert atmosphere; UV-irradiation;	85.3%
With sulfuric acid at 30 - 40℃; for 48h; Temperature; Irradiation;	49.7 g
With sulfuric acid at 25 - 30℃; for 4h; Sealed tube; Irradiation;

: 67-56-1
methanol

: 602-85-7
lysergol

: 86749-38-4
((6aR,9R)-9-Hydroxymethyl-7-methyl-6a,7,8,9-tetrahydro-6H-indolo[4,3-fg]quinolin-4-yl)-methanol

Conditions

Conditions	Yield
With potassium hydroxide at 23℃; electrolysis at 1.2 V vs standard calomel electrode at graphite electrodes;	80%

: 100-07-2
4-methoxy-benzoyl chloride

: 602-85-7
lysergol

: 85893-19-2
O-4-Methoxybenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine Ambient temperature;	80%

: 618-46-2
m-Chlorobenzoyl chloride

: 602-85-7
lysergol

: 85893-12-5
O-3-Chlorbenzoyl-lysergol

Conditions

Conditions	Yield
With pyridine Ambient temperature;	77%

: 2736-40-5
chlorure d'acide ethyl-2 butyrique

: 602-85-7
lysergol

: 31955-01-8
9,10-didehydro-6-methyl-8β-ergolinylmethyl-2-ethylbutyrate

Conditions

Conditions	Yield
dmap In pyridine; chloroform at 0 - 20℃; Acylation;	76%
With pyridine at 70℃;
With pyridine; dmap

: 586-75-4
4-chlorobenzoyl chloride

: 602-85-7
lysergol

: 85893-14-7
O-4-Brombenzoyl-lysergol

Conditions

Conditions	Yield
With pyridine Ambient temperature;	75%

: (R,S)-(+/-)-2-methylbutyrochloride

: 602-85-7
lysergol

: 9,10-didehydro-6-methyl-8β-ergolinylmethyl R,S-2-methylbutyrate

Conditions

Conditions	Yield
dmap In pyridine; chloroform at 0 - 20℃; Acylation;	71%

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 602-85-7
lysergol

: 85893-20-5
O-3,4,5-Trimethoxybenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 100℃; for 1h;	69%

: 27763-54-8
(S)-2-methylbutanoyl chloride

: 602-85-7
lysergol

: 141978-81-6
9,10-didehydro-6-methyl-8β-ergolinylmethyl S-2-methylbutyrate

Conditions

Conditions	Yield
dmap In pyridine; chloroform at 0 - 20℃; Acylation;	67%
With pyridine; dmap

: 122-01-0
4-chloro-benzoyl chloride

: 602-85-7
lysergol

: 85893-13-6
O-4-Chlorbenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine Ambient temperature;	65%

: 1711-05-3
m-anisoyl chloride

: 602-85-7
lysergol

: 85893-18-1
O-3-Methoxybenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 100℃;	63%

: 100-39-0
benzyl bromide

: 602-85-7
lysergol

: 1-benzyl-lysergol

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 3h;	63%

: 1711-06-4
3-Methylbenzoyl chloride

: 602-85-7
lysergol

: 85893-16-9
O-3-Methylbenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 100℃; for 1h;	57%

: 874-60-2
4-methyl-benzoyl chloride

: 602-85-7
lysergol

: 85893-17-0
O-4-Methylbenzoyl-lysergol

Conditions

Conditions	Yield
With pyridine Ambient temperature;	53%

: 393-52-2
2-Fluorobenzoyl chloride

: 602-85-7
lysergol

: 85893-11-4
O-2-Fluorbenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine Ambient temperature;	40%

: 933-88-0
ortho-toluoyl chloride

: 602-85-7
lysergol

: 85893-15-8
O-2-Methylbenzoyl-lysergol-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 100℃;	31%

: 602-85-7
lysergol

: 114249-76-2
(3β)-2,3-dihydrolysergole

Conditions

Conditions	Yield
With triethylsilane; trifluoroacetic acid for 3h; Ambient temperature;	25%

: 602-85-7
lysergol

: 3150-24-1
4-nitrophenyl-β-D-galactopyranoside

: lysergol-β-D-galactoside

Conditions

Conditions	Yield
With 2-hydroxyethanethiol; citric acid; magnesium chloride at 24℃; β-galactosidase from Aspergillus oryzae, K-Pi buffer;	22%

: 602-85-7
lysergol

: 74-88-4
methyl iodide

: 5572-96-3
1-Methyllysergol

Conditions

Conditions	Yield
With potassium amide; ferric nitrate In diethyl ether; ammonia at -50 - -40℃; for 0.5h;	17%
Stage #1: lysergol With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.75h; Stage #2: methyl iodide In 1-methyl-pyrrolidin-2-one for 2h; Solvent;	48.2 g

: 602-85-7
lysergol

: 57-50-1
Sucrose

A: (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol

B: 519-13-1
penniclavine

Conditions

Conditions	Yield
With succinic acid; DL-5-fluorotryptophan In water at 24℃; for 1296h; Claviceps purpurea 88-EP-47;	A 9.2% B n/a

...Expand

: 602-85-7
lysergol

A: (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol

B: 519-13-1
penniclavine

Conditions

Conditions	Yield
With succinic acid; DL-5-fluorotryptophan; Sucrose In water at 24℃; for 1296h; Claviceps purpurea 88-EP-47;	A 9.2% B n/a

: 602-85-7
lysergol

: (9R)-9-acetoxymethyl-4-acetyl-7-methyl-4,5,7,8,9,10-hexahydro-indolo[4,3-fg]quinoline

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid Behandeln des Reaktionsprodukts mit Acetanhydrid in Pyridin;

: 149-30-4
2-Mercaptobenzothiazole

: 602-85-7
lysergol

: 8β-benzothiazol-2-ylsulfanylmethyl-6-methyl-9,10-didehydro-ergoline

Conditions

Conditions	Yield
(i) MeSO2Cl, MeCN, (ii) /BRN= 508810/, HMPT, H2O; Multistep reaction;

: 527-69-5
2-furancarbonyl chloride

: 602-85-7
lysergol

: 87633-44-1
O-Furfuroyl-2'-lysergol

Conditions

Conditions	Yield
With pyridine at 70℃;

Lysergol Specification

The Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8β)- with CAS registry number of 602-85-7 is also known as Lysergol. The systematic name is [(8β)-6-Methyl-9,10-didehydroergolin-8-yl]methanol. Its EINECS registry number is 210-024-5. In addition, the formula is C₁₆H₁₈N₂O and the molecular weight is 254.33. This chemical is a off-white to beige crystalline powder and should be sealed in cool, dry place away from oxidants.

Physical properties about Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8β)- are: (1)ACD/LogP: 1.76; (2)ACD/LogD (pH 5.5): -0.99; (3)ACD/LogD (pH 7.4): 0.63; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 16.01; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 17.4Å²; (12)Index of Refraction: 1.709; (13)Molar Refractivity: 76.23 cm³; (14)Molar Volume: 195.1 cm³; (15)Polarizability: 30.22×10^-24cm³; (16)Surface Tension: 64.3 dyne/cm; (17)Density: 1.3 g/cm³; (18)Flash Point: 235.5 °C; (19)Enthalpy of Vaporization: 76.64 kJ/mol; (20)Boiling Point: 465.8 °C at 760 mmHg; (21)Vapour Pressure: 1.78E-09 mmHg at 25 °C.

When you are using this chemical, please be cautious about it. This chemical at very low levels causes damage to health. It is very toxic by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
1. SMILES: OC[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
2. InChI: InChI=1/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1
3. InChIKey: BIXJFIJYBLJTMK-MEBBXXQBBQ
4. Std. InChI: InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1
5. Std. InChIKey: BIXJFIJYBLJTMK-MEBBXXQBSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	intravenous	320ug/kg (0.32mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 97, 1972.

Product Name

LYSERGOL

Synthetic route

Lysergol Specification

Related Products

Hot Products