485-91-6

Basic information

• Product Name: ALLOCRYPTOPINE
• Synonyms: 3,4-DIMETHOXY-6-METHYL-5,7,8,15-TETRAHYDRO-6H-BENZO[C][1,3]DIOXOLO[4',5':4,5]BENZO[1,2-G]AZECIN-14-ONE;ALLOCRYPTOPINE;ALLOCRYPTOPINE, ALPHA-;ALPHA-ALLOCRYPTOPINE;5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one;5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methylbenzo[e][1,3]dioxolo[4,5-k][3]benzazecin-14(6H)-one;Thalictrimine;C02134
• CAS NO: 485-91-6
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.41
• EINECS: 207-626-5
• Product Categories: Alkaloids
• Mol File: 485-91-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 160～161℃
• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 288.1°C
• Appearance: /
• Density: 1.216g/cm³
• Vapor Pressure: 2.92E-12mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 7.86±0.20(Predicted)
• CAS DataBase Reference: ALLOCRYPTOPINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLOCRYPTOPINE(485-91-6)
• EPA Substance Registry System: ALLOCRYPTOPINE(485-91-6)

Safety Data

• Hazardous Substances Data: 485-91-6(Hazardous Substances Data)

Usage

Description

This alkaloid from Thalictrum minus has been identified as a-Allocryptopine (q.v.).

Uses

Allocryptopine is an alkaloid that displays antiparasitic, antiarrythmic, antithrombotic and anti-inflammatory activity.

References

Kuchkova, Lazur'evskii., Izv. Akad. Nauk. Mold. SSR, Ser. Khim. Bioi., II, 43 (196S)

InChI:InChI=1/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3

Synthetic route

dihydroallocryptopine (14358-63-5, 93527-26-5) → allocryptopine (485-91-6)

Conditions	Yield
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	63%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2h;

canadine (522-97-4, 2086-96-6, 5096-57-1, 29074-38-2) → 12,13-dihydrochelerythrine (6880-91-7) + berberine iodide (4263-84-7) + allocryptopine (485-91-6)

Conditions	Yield
In water at 24℃; for 144h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	A 0.4% B 12.1% C 1.7%

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride (16211-68-0, 24031-76-3, 37791-14-3, 57089-29-9, 59895-76-0, 85888-53-5, 85888-54-6) → 12,13-dihydrochelerythrine (6880-91-7) + allocryptopine (485-91-6)

Conditions	Yield
In water at 24℃; for 192h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	A 1.4% B 6.2%

diazomethane (186581-53-3, 908094-01-9) + 9-demethylallocryptopine (22047-92-3) → allocryptopine (485-91-6)

Conditions	Yield
In diethyl ether

(14Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine 6-oxide (41759-48-2) → allocryptopine (485-91-6)

Conditions	Yield
With hydrogenchloride In acetic acid

9,10,13a-trimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (100176-55-4) + methyl iodide (74-88-4) → allocryptopine (485-91-6)

Conditions	Yield
In methanol

(S)-N-methylcanadine (47474-49-7) → allocryptopine (485-91-6)

Conditions	Yield
With oxygen; NADPH at 30℃; for 0.333333h; tricine buffer, pH 8.5; Yield given;

14-boranyl-3,4-dimethoxy-6-methyl-5,6,7,8,14,15-hexahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine (883867-23-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 2: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

(-)-N-methylcanadine iodide (61774-67-2) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 2: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 3: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 4: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

(+/-)-trans-N-methyl-7,8,13,13a-tetrahydroberberinium iodide (18441-14-0, 26992-09-6, 60384-54-5, 60801-65-2, 61774-67-2, 62860-02-0, 62860-03-1, 92842-79-0, 100176-93-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 2: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 3: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 4: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-11H-benzo[c][1,3]benzodioxolo[5,6-g]azecine (41759-47-1) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 2: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 3: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

canadine (29074-38-2) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetone / 20 °C 2: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 3: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 4: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 5: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 180 mg / acetone / 6 h / 80 °C 2: AgCl / methanol / 1 h / Ambient temperature 3: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme
Multi-step reaction with 4 steps 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 4: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme
Multi-step reaction with 3 steps 1: PhCO3H / CHCl3 2: K2CrO4 / H2O 3: methanol View Scheme

berberine chloride (633-65-8) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.45 g / NaBH4 / methanol / 1 h / Ambient temperature 2: 180 mg / acetone / 6 h / 80 °C 3: AgCl / methanol / 1 h / Ambient temperature 4: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium iodide (18441-14-0, 26992-09-6, 60384-54-5, 60801-65-2, 61774-67-2, 62860-02-0, 62860-03-1, 92842-79-0, 100176-93-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: AgCl / methanol / 1 h / Ambient temperature 2: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme

(+/-)-14-Dihydro-nor-muramin (112333-56-9) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 2: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme

14-hydroxy-3,4-dimethoxy-5,6,7,8,14,15-hexahydrobenzo<1,3>dioxolo<4,5-k><3>benzazecine-6-carbonitrile (112333-20-7) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 3: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme

9,10-dimethoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline-N-oxide (3906-36-3) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CrO4 / H2O 2: methanol View Scheme

9,10-dimethoxy-7-methyl-5,8,12b,13-tetrahydro-6H-[1,3]dioxolo[4'',5'':4,5]benzo[1',2':4,5]azepino[2,1-a]isoindolium; bromide (41759-43-7) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH 2: MCPBA / CHCl3; diethyl ether 3: aq. HCl / acetic acid View Scheme

(Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine (41759-45-9) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: MCPBA / CHCl3; diethyl ether 2: aq. HCl / acetic acid View Scheme

allocryptopine (485-91-6) → allocryptopine N-oxide (87264-52-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 24h; Ambient temperature;	86%

allocryptopine (485-91-6) → 13-oxoallocryptopine (15211-10-6)

Conditions	Yield
With mercury(II) diacetate In water; acetic acid at 75℃; for 4.5h;	41%

allocryptopine (485-91-6) → 12,13-dihydrochelerythrine (6880-91-7)

Conditions	Yield
In water at 24℃; for 168h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	33.4%
Multi-step reaction with 2 steps 1: 86 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / Ambient temperature 2: 2 percent / 2.) NaBH4 / methanol / 1.) methanol, irradiation; 2.) methanol View Scheme
With recombinant Eschscholzia californica P450 CYP82N2v2; NADPH In aq. buffer at 30℃; pH=7.6; Kinetics; Enzymatic reaction;

allocryptopine (485-91-6) → 7,8-dimethoxy-2-methyl-3-(6-vinyl-benzo[1,3]dioxol-5-yl)-1,2-dihydro-isoquinoline (28332-37-8)

Conditions	Yield
(i) PCl3, (ii) KOH, MeOH; Multistep reaction;
Multi-step reaction with 2 steps 1: PCl3 2: KOH / methanol View Scheme

allocryptopine (485-91-6) → N-methyldihydroberberine chloride (26668-90-6)

Conditions	Yield
With phosphorus trichloride

trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + allocryptopine (485-91-6) → N-methyldihydroberberine chloride (26668-90-6)

Conditions	Yield
α-allocryptopine;

sulfuric acid (7664-93-9) + allocryptopine (485-91-6) + sodium amalgam → dihydroallocryptopine

Conditions	Yield
α-allocryptopine;

allocryptopine (485-91-6) → C27H29NO8

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) PCl3, (ii) KOH, MeOH 2: benzene / Irradiation View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 22047-92-3 9-demethylallocryptopine 
• 41759-48-2 (14Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine 6-oxide 
• 100176-55-4 9,10,13a-trimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 
• 74-88-4 methyl iodide 
• 3906-36-3 9,10-dimethoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline-N-oxide 
• 41759-45-9 (Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine 
• 41759-43-7 9,10-dimethoxy-7-methyl-5,8,12b,13-tetrahydro-6H-[1,3]dioxolo[4'',5'':4,5]benzo[1',2':4,5]azepino[2,1-a]isoindolium; bromide 
• 112333-20-7 14-hydroxy-3,4-dimethoxy-5,6,7,8,14,15-hexahydrobenzo<1,3>dioxolo<4,5-k><3>benzazecine-6-carbonitrile 
• 112333-56-9 (+/-)-14-Dihydro-nor-muramin 
• 18441-14-0 (+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium iodide 
• 633-65-8 berberine chloride 
• 29074-38-2 canadine 
• 41759-47-1 3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-11H-benzo[c][1,3]benzodioxolo[5,6-g]azecine 

Downstream Products

• 2086-83-1 berberine 

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