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602-85-7

Basic Information
CAS No.: 602-85-7
Name: Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8β)-
Molecular Structure:
Molecular Structure of 602-85-7 (Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8β)-)
Formula: C16H18N2O
Molecular Weight: 254.33
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;
EINECS: 210-024-5
Density: 1.3 g/cm3
Melting Point: 248°C
Boiling Point: 465.8 °C at 760 mmHg
Flash Point: 235.5 °C
Solubility:
Appearance: Off-white to beige crystalline powder
Hazard Symbols: VeryT+
Risk Codes: 26/27/28
Safety: 26-36/37/39-45
Transport Information: UN 1544
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
ConditionsYield
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
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.166667h;A 24%
B 49%
478-91-1

Lysergen

602-85-7

lysergol

Conditions
ConditionsYield
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
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
elymoclavine

elymoclavine

602-85-7

lysergol

Conditions
ConditionsYield
With sodium butanolate; butan-1-ol
elymoclavine

elymoclavine

A

602-85-7

lysergol

B

isolysergol, lysergene

isolysergol, lysergene

Conditions
ConditionsYield
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

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
ConditionsYield
at 140℃;
519-12-0

(+)-setoclavine

602-85-7

lysergol

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

C25H26N2O4S

602-85-7

lysergol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine Ambient temperature;80%
618-46-2

m-Chlorobenzoyl chloride

602-85-7

lysergol

85893-12-5

O-3-Chlorbenzoyl-lysergol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine Ambient temperature;65%
1711-05-3

m-anisoyl chloride

602-85-7

lysergol

85893-18-1

O-3-Methoxybenzoyl-lysergol-hydrochlorid

Conditions
ConditionsYield
With pyridine at 100℃;63%
100-39-0

benzyl bromide

602-85-7

lysergol

1-benzyl-lysergol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine Ambient temperature;53%
393-52-2

2-Fluorobenzoyl chloride

602-85-7

lysergol

85893-11-4

O-2-Fluorbenzoyl-lysergol-hydrochlorid

Conditions
ConditionsYield
With pyridine Ambient temperature;40%
933-88-0

ortho-toluoyl chloride

602-85-7

lysergol

85893-15-8

O-2-Methylbenzoyl-lysergol-hydrochlorid

Conditions
ConditionsYield
With pyridine at 100℃;31%
602-85-7

lysergol

114249-76-2

(3β)-2,3-dihydrolysergole

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With succinic acid; DL-5-fluorotryptophan In water at 24℃; for 1296h; Claviceps purpurea 88-EP-47;A 9.2%
B n/a
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
(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
ConditionsYield
With pyridine at 70℃;
Downstream Products
18051-16-6
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  • Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8b)- CAS602-85-7

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    602-85-7

    Ergoline-8-methanol,9,10-didehydro-6-methyl-, (8b)- CAS602-85-7

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    602-85-7 Appearance:white powder Storage:Store at a temperature of 2-10 °C. Package:According to customer requirements Application:medicine Port:Any port in China

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    602-85-7

    LYSERGOL 602-85-7

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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.