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Alkaloids

Protopine

Also known as Corydinine, Biflorine, Macleyine

CAS 130-86-9Formula C20H19NO5Molar mass 353.37 g/molEC 204-999-6
GHS signal word: Danger. Pictograms: Acute toxicity (severe), Harmful or irritant 23 suppliers listed
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Protopine chemical structure, C20H19NO5, CAS 130-86-9
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Monoclinic prisms from alcohol + chloroform
Melting point
208 °C
Density
1.399 (calc)
Solubility
Practically insoluble in water
HS code
293979
Category
Alkaloids
Illustrative photo, assorted laboratory chemical bottles and jars on a laboratory bench
Typical packagingIllustrative packaging image, not the actual product

What is Protopine?

Plain description, key identifiers and synonyms

Protopine is a dibenzazecine alkaloid isolated from Fumaria vaillantii. It has a role as a plant metabolite.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
CAS number
130-86-9 CAS number cross-checked
EC number
204-999-6
Molecular formula
C20H19NO5
UNII
UIW569HT35
MDL number
MFCD00022322
InChIKey
GPTFURBXHJWNHR-UHFFFAOYSA-N
InChI
InChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
SMILES (canonical and isomeric)
CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3

Synonyms

  • Corydinine
  • Biflorine
  • Macleyine
  • Fumarine
  • Protopin
  • 7-Methyl-2,3:9,10-bis(methylenedioxy)-7,13a-secoberbin-13a-one
  • 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-
  • Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-
  • 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one
  • Bis(1,3)benzodioxolo(4,5-C:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo(15.7.0.0^(4,12).0^(6,10).0^(18,22))tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo(15.7.0.04,12.06,10.018,22)tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo(15.7.0.04,12.06,10.018,22)tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one
  • Hypercorine
  • 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[5',4':4,5]benzo[1,2-g]azecin-15(16H)-one
  • 4,6,7,14-Tetrahydro-5-methylbis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one
  • 7-methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one
  • 7-Methyl-6,8,9,16-tetrahydrodi[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one
  • 7-methyl-4H,6H,8H,9H,12H,16H-1,3-dioxoleno[4''',5'''-3'',4'']benzo[1'',2''-8', 9']azecino[5',4'-2,1]benzo[4,5-d]1,3-dioxolan-15-one
  • Protopine (Standard)
  • Alk-3
  • Protopine (Corydinine)
  • Protopine, analytical standard
Show all 33 synonyms
  • ACon1_001550
  • HSCI1_000268
  • 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[5',4':4,5]benzo[1,2-g]azecin-
  • 7-methyl-6,8,9,16-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[5',4':4,5]benzo[1,2-g]azecin-15(7H)-one
  • 7-methyl-2,3:9,10-bis[methylenebis(oxy)]-7,13a-secoberbin-13a-one
  • 7-Methyl-6,8,9,16-tetrahydrodi[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one #
  • 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(17),4(12),5,10,18(22),23-hexaen-3-one
  • 7-Methyl-6,8,9,16-tetrahydro-4H,12H-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Monoclinic prisms from alcohol + chloroformexp.
Melting point
208 °Cexp.
Density
1.399 (calc)exp.
Solubility
Practically insoluble in waterexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
353.37 g/molcalc.
Exact mass
353.1263 Dacalc.
LogP (octanol/water)
2.56calc.
Topological polar surface area
57.23 Ųcalc.
Hydrogen bond donors
0calc.
Hydrogen bond acceptors
6calc.
Rotatable bonds
0calc.
Heavy atoms
26calc.
Rings
5calc.
Aromatic rings
2calc.
Fraction sp3 carbons
0.35calc.
Formal charge
0calc.
Stereocentres
0calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C1Cc2ccc3c(c2CNCCc2cc4c(cc21)OCO4)OCO3

O=C1Cc2ccc3c(c2CNCCc2cc4c(cc21)OCO4)OCO3

5 rings, 25 atoms.

7 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS06: Acute toxicity (severe)
Acute toxicity (severe)
GHS07: Harmful or irritant
Harmful or irritant

Hazard statements

  • H301Toxic if swallowed.
  • H302Harmful if swallowed.
Precautionary statements (8)
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P301 + P316If swallowed: Get emergency medical help immediately.
  • P301 + P317If swallowed: Get medical help.
  • P321Specific treatment (see supplemental first aid instructions on the label).
  • P330Rinse mouth.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Protopine suppliers

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All 23 suppliers
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Where suppliers are based

23 suppliers in 6 countries

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Protopine price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Ca2+ channel blocker and antiplatelet agent (Protopine hydrochloride).

Pharmacological actions

  • Analgesics, Opioid
  • Histamine H1 Antagonists
  • Platelet Aggregation Inhibitors

Roles

  • eukaryotic metabolite
  • metabolite
  • plant metabolite

How it is made

From opium ... also from the herb Fumaria officinalis L., Chelidonium majus L., and many other Papaveraceae and Fumariaceae.

Protopine hydrochloride (5,6,14,14a-tetrahydro-14a-hydroxy-7-methyl-8H-bis[1,3]benzodioxolo[5,6-a:4,5-g]quinolizinium chloride, C20H20NO5(+)-Cl(-)) is the salt of the isoquinoline alkaloid protopine. It is formed by the action of dilute hydrochloric acid on the protopine free base. The N-methyl and hydroxyl groups are in a trans configuration in the quinolizine ring and the central quinolizine N-C bond is unusually long [1.579 (2) A]. The crystal is a racemate. (Protopine hydrochloride)

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Protopine is traded under.

HS 2939.79Indicative HS code

Alkaloids of vegetal origin, other than cocaine, ecgonine, salts, esters and other derivatives, not elsewhere…

World exports in 2024
$701M
+18.9% vs 2023, imports $830M
2019 to 2024
Top exporters
  1. Switzerland * partner reported25.3%
  2. Germany21.4%
  3. India * partner reported14.9%
Top importers
  1. United States20.9%
  2. Germany14.7%
  3. Italy14.6%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Protopine is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Protopine, based on the data on this page

What is Protopine?

Protopine is a dibenzazecine alkaloid isolated from Fumaria vaillantii. It has a role as a plant metabolite.

What is the CAS number of Protopine?

The CAS registry number of Protopine is 130-86-9.

What is the molecular formula and weight of Protopine?

The molecular formula of Protopine is C20H19NO5 and its molar mass is 353.37 g/mol.

What is Protopine used for?

Ca2+ channel blocker and antiplatelet agent (Protopine hydrochloride).

Is Protopine hazardous?

Protopine carries the GHS signal word "Danger". Main hazards: toxic if swallowed, harmful if swallowed. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Protopine?

Protopine is usually classified under HS code 293979 (Alkaloids, natural or reproduced by synthesis, and their salts, ethers, esters and other…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Protopine?

CompoundList lists 23 suppliers of Protopine in China, United States, Germany, United Kingdom and 2 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Protopine?

Suppliers quote Protopine on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Protopine

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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