Table 2 Structure of CBD analogs and summary of effect of modification to different positions on antimicrobial activity against MRSA and N. gonnorrhoeae (MIC, μg mL−1, n = 4).

From: The antimicrobial potential of cannabidiol

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Compound name

Core Scaffold

R1

R2

R3

R4

R5

S. aureus MRSA ATCC 43300

N. gonorrhoeae ATCC 19424

 

Control: Vancomycin

      

1

nd

 

Control: Colistin

      

nd

32

 

Control: Daptomycin

      

1–2

>64

 

Control: Clindamycin

      

>64

1

 

Control: Mupirocin

      

0.125–0.5

≤0.03–0.06

1

Cannabidiol

A

nPr

H

OH

OH

Me

1–2

0.125–2

2

7-hydroxycannabidiol

A

nPr

H

OH

OH

CH2OH

16

0.25–2

3

MTC-005

A

nPr

H

OH

OH

CH2OMe

16

4–16

4

7-nor-7-carboxycannabidiol

A

nPr

H

OH

OH

CO2H

64–>64

0.5–2

5

MTC-002

A

nPr

H

OH

OH

CONHMe

16

2–4

6

Cannabidivarin

A

Me

H

OH

OH

Me

2–4

≤0.03–0.5

7

7-nor-7-hydroxymethyl-cannabidivarin

A

Me

H

OH

OH

CH2OH

64

>64

8

7-nor-7-carboxy-cannabidivarin

A

Me

H

OH

OH

CO2H

>64

2–16

9

MTC-007

A

nPent

H

OH

OH

Me

0.5–2

0.5–4

10

MTC-017

A

(CH2)2Ph

H

OH

OH

Me

2

0.5–4

11

MTC-011

A

nPr

H

H

OH

Me

64–>64

1–8

12

MTC-012

A

nPr

H

OMe

OH

Me

>64

8–32

13

MTC-013

A

nPr

H

OMe

OMe

Me

>64

>64

14

Cannabidiolic acid (CBDA)

A

nPr

CO2H

OH

OH

Me

16–32

1–2

15

MTC-018

B

nPent

1–2

1–2

16

MTC-008

B

(CH2)2Ph

2–4

1–4

17

MTC-014

C

0.25–0.5

0.25–0.5

18

MTC-009

D

1–2

0.5–2

19

Tetrahydrocannabivarin (THCV)

E

Me

H

64

16

20

Tetrahydrocannabivarinic acid (THCVA)

E

Me

CO2H

32–64

4–16

21

(−)-Δ9-THC

E

nPr

H

4–8

4–8

22

Δ9-tetrahydrocannabinolic acid A (THCA-A)

E

nPr

CO2H

8

0.5–8

23

(−)-Δ8-THC

F

4–8

2–4

24

Cannabinolic acid A (CBNA)

G

4–16

0.25–4

25

Cannabigerol (CBG)

H

H

4–8

1–2

26

Cannabigerolic acid (CBGA)

H

CO2H

2–4

1–2